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[ CAS No. 79836-78-5 ] {[proInfo.proName]}

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Chemical Structure| 79836-78-5
Chemical Structure| 79836-78-5
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Quality Control of [ 79836-78-5 ]

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Product Details of [ 79836-78-5 ]

CAS No. :79836-78-5 MDL No. :MFCD03840442
Formula : C7H9NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :ORCQTMZHDQSNOJ-UHFFFAOYSA-N
M.W : 171.22 Pubchem ID :12808791
Synonyms :

Calculated chemistry of [ 79836-78-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.43
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.17
TPSA : 67.43 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.21
Log Po/w (XLOGP3) : 1.91
Log Po/w (WLOGP) : 1.63
Log Po/w (MLOGP) : 0.37
Log Po/w (SILICOS-IT) : 2.64
Consensus Log Po/w : 1.75

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.24
Solubility : 0.978 mg/ml ; 0.00571 mol/l
Class : Soluble
Log S (Ali) : -2.95
Solubility : 0.192 mg/ml ; 0.00112 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.16
Solubility : 1.19 mg/ml ; 0.00697 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.46

Safety of [ 79836-78-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 79836-78-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 79836-78-5 ]

[ 79836-78-5 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 79836-78-5 ]
  • [ 40004-69-1 ]
YieldReaction ConditionsOperation in experiment
70% b) 2-Methyl-thiazole-5-carboxylic acid To a stirred solution of <strong>[79836-78-5]2-methyl-thiazole-5-carboxylic acid ethyl ester</strong> (1.3 g, 8.0 mmol) in dioxane (12 mL) at room temperature was added NaOH (2N, 12 mL). After 1 h the reaction mixture was neutralized with HCl (IN, 12 mL), then filtered and the collected solid dried in vacuo to give the title compound (758 mg, 70percent) as an off white solid. MS: m/e = 142.0 [M-H]".
41% With lithium hydroxide monohydrate; water; In tetrahydrofuran; at 20℃; for 16h; To a stirred solution of compound 97 (41 g, 239.76 mmol) in THF: H2O (7: 1, 400 mL) was added lithium hydroxide monohydrate (29.49 g, 719.29 mmol) at room temperature and stirred for 16 h. The reaction was monitored by TLC. After completion of the reaction, the volatiles were removed in vacuo. The residue was diluted with water and acidified with 2 N HCl to pH~2 and extracted using EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford compound 98 (14 g, 41percent) as an off-white solid. TLC: 20percent EtOAc/ hexanes (Rf: 0.1); 1H NMR (DMSO-d6, 400 MHz): delta 13.29 (br.s, 1H), 8.16 (s, 1H), 2.69 (s, 3H); LCMS Calculated for C5H5NO2S: 143.00; Observed: 144.1 (M+1)+.
Ethyl 2-methyl-1,3-thiazole-5-carboxylate [e.g. available from Interchim S.A.] (61 mg) in ethanol (1 ml) was treated with aqueous sodium hydroxide (2M, 0.706 ml). The clear solution was stirred at room temperature for 18 h and then treated with aqueous hydrochloric acid (2M, 0.54 ml). The solution was blown down to dryness and the residual solid dried under vacuum over phosphorus pentoxide. The solid was then suspended in dry dichloromethane (1 ml) and treated at 20° C. with oxalyl chloride (0.032 ml) and DMF (1 drop). The mixture was stirred at room temperature for 30 mins and was then added dropwise to a solution of Intermediate 16 (98 mg) in anhydrous acetonitrile (2 ml). DIPEA (0.064 ml) was added and the solution stirred at room temperature for 20 h. The mixture was diluted with dichloromethane (15 ml), washed with dilute aqueous sodium chloride (2.x.15 ml) and blown down to dryness. The residue was purified by mass directed autoprep HPLC to give a film which was further purified using an SPE cartridge (2 g, aminopropyl) which had been pre-washed with methanol. Elution with methanol gave Example 311 as a white solid (87 mg). LCMS showed MH+=429; TRET=1.94 min.
Synthesis of (E) To a 0° C. solution of <strong>[79836-78-5]ethyl 2-methyl-thiazole-5-carboxylate</strong> (15 g, 88 mmol) in tetrahydrofuran (50 mL) was added aqueous sodium hydroxide solution (5 N, 50 mL) over 10 minutes, and the resulting solution was stirred at room temperature for another 2 hours. It was then acidified with hydrochloric acid (2 N) to pH=1 and extracted with tetrahydrofuran (3*100 mL). The combined organic layers were washed with brine (30 mL) and dried over sodium sulfate. Most of the solvents were removed under reduced pressure and the residue was lyophilized to afford Compound (E) (14 g).
Example 311 N-[1,6-diethyI-4-(tetrahydro-2H-pyran-4-yIamino)-1H- pyrazoIo[3,4-b]pyridin-5-yl]methyl}-2-methyI-1,3-thiazole-5-carboxamideEthyl 2-methyl-1 ,3-thiazole-5-carboxylate [e.g. available from lnterchim S.A.] (61 mg) in ethanol (1ml) was treated with aqueous sodium hydroxide (2M, 0.706ml). The clear solution was stirred at room temperature for 18h and then treated with aqueous hydrochloric acid (2M, 0.54ml). The solution was blown down to dryness and the residual solid dried under vacuum over phosphorus pentoxide. The solid was then suspended in dry dichloromethane (1ml) and treated at 20°C with oxalyl chloride (0.032ml) and DMF (1 drop). The mixture was stirred at room temperature for 30mins and was then added dropwise to a solution of Intermediate 16 (98mg) in anhydrous acetonitrile (2ml). DIPEA (0.064ml) was added and the solution stirred at room temperature for 2Oh. The mixture was diluted with dichloromethane (15ml), washed with dilute aqueous sodium chloride (2 x 15ml) and blown down to dryness. The residue was purified by mass directed autoprep HPLC to give a film which was further purified using an SPE cartridge (2g, aminopropyl) which had been pre-washed with methanol. Elution with methanol gave Example 311 as a white solid (87mg). LCMS showed MH+ =
14 g With water; sodium hydroxide; In tetrahydrofuran; at 0 - 20℃; for 2.16h; To a 0° C. solution of <strong>[79836-78-5]ethyl 2-methyl-thiazole-5-carboxylate</strong> (15 g, 88 mmol) in tetrahydrofuran (50 mL) was added aqueous sodium hydroxide solution (5 N, 50 mL) over 10 minutes, and the resulting solution was stirred at room temperature for another 2 hours. It was then acidified with hydrochloric acid (2 N) to pH=1 and extracted with tetrahydrofuran (3*100 mL). The combined organic layers were washed with brine (30 mL) and dried over sodium sulfate. Most of the solvents were removed under reduced pressure and the residue was lyophilized to afford Compound (E) (14 g).
14 g With water; sodium hydroxide; In tetrahydrofuran; water; at 0 - 20℃; for 2.16667h; To a 0°C. solution of <strong>[79836-78-5]ethyl 2-methyl-thiazole-5-carboxylate</strong> (15 g, 88 mmol) in tetrahydrofuran (50 ml) was added aqueous sodium hydroxide solution (5 N, 50ml) over 10 minutes, and the resulting solution was stirred at room temperature for another 2 hours. It was then acidified with hydrochloric acid (2 N) to pH=1 and extracted with tetrahydrofuran (3x100 ml). The combined organic layers were washed with brine (30 mL) and dried over sodium sulfate. Most of the solvents were removed under reduced pressure and the residue was lyophilized to afford Compound (E) (14g).
14 g With water; sodium hydroxide; In tetrahydrofuran; at 0℃; for 2.16667h; To a 0° C. solution of <strong>[79836-78-5]ethyl 2-methyl-thiazole-5-carboxylate</strong> (15 g, 88 mmol) in tetrahydrofuran (50 mL) was added aqueous sodium hydroxide solution (5 N, 50 mL) over 10 minutes, and the resulting solution was stirred at room temperature for another 2 hours. It was then acidified with hydrochloric acid (2 N) to pH=1 and extracted with tetrahydrofuran (3×100 mL). The combined organic layers were washed with brine (30 mL) and dried over sodium sulfate. Most of the solvents were removed under reduced pressure and the residue was lyophilized to afford Compound (E) (14 g).

  • 2
  • [ 79836-78-5 ]
  • [ 99979-78-9 ]
  • 3
  • [ 79836-78-5 ]
  • [ 409316-66-1 ]
YieldReaction ConditionsOperation in experiment
With hydrazine; In ethanol; for 12h;Heating / reflux; Preparation 9: 2-methyl-1,3-thiazole-5-carbohydrazide; EPO <DP n="44"/>The title compound was prepared in analogy to the method described in Preparation 4 starting from ethyl 2-methyl-1 ,3-thiazole-5-carboxylate (0.5g) and used without further purification. Ethanol was used instead of methanol. MS (mlz): 158.1 [MH]+.
  • 4
  • [ 79836-78-5 ]
  • 2-methyl-thiazole-5-carbonyl azide [ No CAS ]
  • 5
  • [ 79836-78-5 ]
  • [ 56012-38-5 ]
YieldReaction ConditionsOperation in experiment
83% With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 16.25h;Inert atmosphere; To a stirred suspension of lithium aluminium hydride (3.1 g, 93.56 mmol) in dry THF (10 mL) under inert atmosphere was added compound 63 (8 g, 46.78 mmol) in dry THF (50 mL) dropwise for 15 mm at 0 °C; warmed to RT and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was cooled to 0 °C, quenched with15percent aqueous sodium hydroxide solution (10 mL), filtered through celite and washed withEtOAc (3 x 100 mL). The filtrate was dried over sodium sulfate, filtered and concentrated invacuo to afford compound 64 (5 g, 83percent) as an off-white solid. TLC: 50percent EtOAc/ hexanes (Rf:0.3). LC-MS: 97.32percent; 130.22 (M+1) (column; X-select CSH C18, (50 x 3.0 mm, 2.5 jim); RT0.65 mm. 2.5 mM Aq. NH4OAc: ACN: 0.8 mL/min).
78% In chloroform; B. 5-(Hydroxymethyl)-2-methylthiazole Using the procedure of Example 1P, but replacing ethyl thiazole-5-carboxylate with crude ethyl 2-methylthiazole-5-carboxylate provided, after silica gel chromatography using 3percent then 5percent methanol in chloroform, the desired compound, Rf 0.27, (4percent methanol in chloroform) in 78percent yield. 1 H NMR (CDCl3)delta2.32 (br, 1H), 2.70 (s, 3H), 4.80 (s, 2H), 7.46 (s, 1H). Mass spectrum: (M+H)+ =130.
Step 1: Intermediate 15-a To a solution of ethyl 2-methylthiazole-5-carboxylate (5.82 g, 34.0 mmol) in THF (170 ml), cooled to 0 °C, was added a 1.0M solution of LiAIH4 in THF (34.0 ml, 34.0 mmol) and the reaction was slowly warmed to room temperature and stirred overnight. Water (1.3 ml) was slowly added, followed by 15percent NaOH (1.3 ml_). The solution was stirred for 2 hours at room temperature then filtered over celite. The filtrate was concentrated under reduced pressure to provide intermediate 15-a as a yellow oil.
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2h; To a solution of intermediate 7-c (22.2 g, 130.0 mmol) in THF (430 ml) cooled to 0°C was added a 1.0 M solution LiAIH4 in THF (91.0 ml, 91.0 mmol). The solution was slowly warmed to room temperature and stirred for 2 hours. Water (3.5 ml) was slowly added, followed by 3.5 ml 15percent NaOH (3.5 ml) and water (10.5 ml) and the mixture was stirred for 1 hour. The reaction was filtered through celite and the filtrate collected. Volatiles were removed in vacuo to provide intermediate 7-d as a yellow oil.
Step 3: Intermediate 5-d; To a solution of intermediate 5-c (22.2 g, 130.0 mmol) in THF (430 ml) cooled to 0°C was added a 1.0 M solution LiAIH4 in THF (91.0 ml, 91.0 mmol) and the solution was slowly warmed to room temperature and stirred for 2 hours. Water (3.5 ml) was slowly added, followed by 3.5 ml lSpercent NaOH (3.5 ml) and water (10.5 ml) and the mixture was stirred for 1 hour. The reaction was filtered over celite and volatiles were removed under reduced pressure to provide intermediate 5-d as yellow oil.
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere; To a stirred solution of ethyl 2-methylthiazole-5-carboxylate (1 eq) in dry THF (5 mL) at 0
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2h; Step 4: Intermediate 29-d [0172] To a solution of intermediate 29-c (22.2 g, 130.0 mmol) in THF (430 ml) cooled to 0° C. was added a 1.0 M solution of LiAlH4 in THF (91.0 ml, 91.0 mmol) and the solution was slowly warmed to room temperature and stirred for 2 hours. Water (3.5 ml) was slowly added, followed by 3.5 ml 15percent NaOH (3.5 ml) and water (10.5 ml) and the mixture was stirred for 1 hour. The reaction was filtered over celite and volatiles were removed in vacuo to provide intermediate 29-d as yellow oil.
12g With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 18h; Step 1: Synthesis of 2-methyl-5-hydroxymethylthiazole: At room temperature, lithium aluminum hydride (8.88g, 234mmol) was dispersed in anhydrous tetrahydrofuran (THF, 100mL). The resulting mixture was cooled to 0-5°C in an ice-water bath. To the cooled mixture was dropwise added a solution of 2-methyl-5-ethoxyformylthiazole (20g,117mmol) in anhydrous tetrahydrofuran (THF, 100mL). After the completion of the dropwise addition, the reaction mixture was naturally warmed to room temperature, and was stirred for 18 hours at room temperature. To the reaction mixture was dropwise added water (10mL) at 0-5°C. After the completion of the dropwise addition, the resulting mixture was filtered. The filtrate was concentrated to produce a yellow oily substance (12g), which was directly used in the next step.

  • 7
  • [ 62-55-5 ]
  • [ 33142-21-1 ]
  • [ 79836-78-5 ]
YieldReaction ConditionsOperation in experiment
47% In benzene; for 4h;Reflux; Inert atmosphere; Example 72- [2-(5-Methyl-3-phenyl-isoxazol-4-yl)-ethyl] -thiazole-5-carboxylic acid isopropyl- amidea) 2-Methyl-thiazole-5-carboxylic acid ethyl esterTo a stirred solution of ethyl 2-chloro-2-formyl acetate (5.0 g, 33 mmol) in benzene (50 mL) at reflux under argon was added thioamide (2.5 g, 33 mmol). After 4 h the reaction mixture was cooled, diluted with water (50 mL) and neutralized to pH 7 with a saturated solution of sodium hydro gencarbonate. The reaction mixture was extracted with ethyl acetate then the combined extracts were washed with water and brine, then dried, filtered and concentrated in vacuo. Purification by chromatography (silica, 0 to 50percent ethyl acetate in heptane) gave the title compound (2.68 g, 47percent) as a yellow liquid. MS: m/e = 172.0 [M+H]+.
35% With magnesium sulfate; In ethanol; for 24h;Inert atmosphere; Reflux; To a stirred solution of <strong>[33142-21-1]ethyl 2-chloro-3-oxopropanoate</strong> 61 (26 g, 173.33 mmol) in ethanol (200 mL) under argon atmosphere were added ethanethioamide 62 (10 g, 133.33 mmol), dry magnesium sulfate (10 g) at RT and heated to reflux for 24 h. The reaction was monitored by TLC; after completion of the reaction, the volatiles were removed in vacuo, diluted with EtOAc (500 mL). The combined organic extracts were washed with saturated sodium bicarbonatesolution (2 x 200 mL), brine (200 mL), dried over sodium sulfate, filtered and concentrated invacuo to obtain the crude. The crude was purified through flash column chromatography using6percent EtOAc/ hexanes to afford compound 63 (8 g, 35percent) as brown syrup. TLC: 25percent EtOAc/hexanes (Rf: 0.7); ?H-NMR (DMSO-d6, 500 MHz): oe 8.24 (s, 1H), 4.27 (q, J = 7.2 Hz, 2H),2.70 (s, 3H), 1.27 (t, J = 7.1 Hz, 3H).
33% With magnesium sulfate; In ethanol; at 80℃; for 16h;Inert atmosphere; To a stirring solution of compound 96 (110 g, 733.33 mmol) in ethanol (1.2 L) under Ar atmosphere were added ethanethioamide (54.99 g, 733.33 mmol) and anhydrous magnesium sulfate (55 mg, 454.66 mmol) at room temperature, followed by heating to 80 oC for 16 h. The reaction was monitored by TLC. After completion of the reaction, the volatiles were removed in vacuo. The residue was diluted with water and extracted using EtOAc. The organic extract was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 10percent EtOAc/hexanes to afford compound 97 (41 g, 33percent) as thick syrup. TLC: 20percent EtOAc/ hexanes (Rf: 0.3); 1H NMR (400 MHz, DMSO-d6): delta 8.26 (s, 1H), 4.29 (q, J = 7.2 Hz, 2H), 2.71 (s, 3H), 1.29 (t, J = 7.1 Hz, 3H); LCMS Calculated for C7H9NO2S: 171.04; Observed: 172.1 (M+1)+.
In toluene; at 90℃; Step 2: Intermediate 29-c To a solution of <strong>[33142-21-1]ethyl 2-chloro-3-oxopropanoate</strong>, 29-b (34.7 g, 230 mmol), in toluene (250 ml) was added thioacetamide (26.0 g, 346.0 mmol), the reaction was stirred at 90°C overnight and then cooled to room temperature, diluted with water (300 mL) and then neutralized to pH 7 with a saturated aqueous solution of NaHC03. Ethyl acetate was added, the organic layer was separated, washed with brine, dried over MgS04, filtered and concentrated under reduced pressure. Purification by silica gel chromatography provided intermediate 29-c as beige oil.
In toluene; at 90℃; Step 2: Intermediate 7-cTo a solution of <strong>[33142-21-1]ethyl 2-chloro-3-oxopropanoate</strong>, 7-b (34.7 g, 230 mmol) in toluene (250 ml) was added thioacetamide (26.0 g, 346.0 mmol). The reaction was stirred at 90°C overnight and then cooled to room temperature, diluted with water (300 mL) and then neutralized to pH=7 with saturated aqueous NaHCO3. Ethyl acetate was added, the organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by silica gel chromatography provided intermediate 7-c as a beige oil.
In toluene; at 90℃; Step 2: Intermediate 5-c<BOLD>: </BOLD>To a solution of <strong>[33142-21-1]ethyl 2-chloro-3-oxopropanoate</strong> 5-b (34.7 g, 230 mmol) in toluene (250 ml) was added thioacetamide (26.0 g, 346.0 mmol). The reaction was stirred at 90°C overnight and then cooled to room temperature, diluted with water (300 mL) and then neutralized to PH=7 with a saturated aqueous solution of NaHCO3. Ethyl acetate was added, the organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by silica gel chromatography provided intermediate 5-c as beige oil
In toluene; at 90℃; Step 2: Intermediate 29-c [0171] To a solution of <strong>[33142-21-1]ethyl 2-chloro-3-oxopropanoate</strong>, 29-b (34.7 g, 230 mmol), in toluene (250 ml) was added thioacetamide (26.0 g, 346.0 mmol), the reaction was stirred at 90° C. overnight and then cooled to room temperature, diluted with water (300 mL) and then neutralized to pH 7 with a saturated aqueous solution of NaHCO3. Ethyl acetate was added, the organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by silica gel chromatography provided intermediate 29-c as beige oil.

  • 9
  • [ 62-55-5 ]
  • 2-chloro-3<i>t</i>-hydroxy-acrylic acid ethyl ester [ No CAS ]
  • [ 79836-78-5 ]
  • 10
  • [ 62-55-5 ]
  • [ 4504-12-5 ]
  • 3-Phenyl-2-[2-thioxo-prop-(Z)-ylidene]-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester [ No CAS ]
  • [ 79836-78-5 ]
  • 11
  • [ 79836-78-5 ]
  • [ 82190-77-0 ]
  • 12
  • [ 79836-78-5 ]
  • [ 82190-74-7 ]
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