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[ CAS No. 704-91-6 ] {[proInfo.proName]}

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Chemical Structure| 704-91-6
Chemical Structure| 704-91-6
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Product Details of [ 704-91-6 ]

CAS No. :704-91-6 MDL No. :MFCD06804571
Formula : C8H6N2O2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :DNCVTVVLMRHJCJ-UHFFFAOYSA-N
M.W : 162.15 Pubchem ID :16227938
Synonyms :

Calculated chemistry of [ 704-91-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 43.05
TPSA : 65.98 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.39
Log Po/w (XLOGP3) : 1.76
Log Po/w (WLOGP) : 1.26
Log Po/w (MLOGP) : 0.72
Log Po/w (SILICOS-IT) : 1.38
Consensus Log Po/w : 1.1

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.44
Solubility : 0.585 mg/ml ; 0.0036 mol/l
Class : Soluble
Log S (Ali) : -2.76
Solubility : 0.28 mg/ml ; 0.00173 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.27
Solubility : 0.863 mg/ml ; 0.00532 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.27

Safety of [ 704-91-6 ]

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

Application In Synthesis of [ 704-91-6 ]

* 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 [ 704-91-6 ]

[ 704-91-6 ] Synthesis Path-Downstream   1~14

  • 2
  • [ 478169-77-6 ]
  • [ 704-91-6 ]
YieldReaction ConditionsOperation in experiment
800 mg (97%) With potassium tert-butylate; In dimethyl sulfoxide; To a stirred solution of potassium tert-butoxide (8.1 g, 73 mmol) in DMSO (30 mL) was added a solution of 3-[(E)-(tert-butylthio)diazenyl]-4-methylbenzoic acid (1.9 g, 7.3 mmol) at RT. The mixture was stirred overnight, followed by the adition of ice water. The aqueous layer was extracted with ethyl acetate. The organic layer was dicarded. The pH of the aqueous layer was adjusted to 4-5 with aqueous 1N HCl. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford 800 mg (97percent) of 1H-indazole-6-carboxylic acid as a tan solid: 1H NMR (400 MHz. DMSO-d6) delta 13.4, 13.0, 8.2, 8.1, 7.9, 7.7.
  • 3
  • [ 704-91-6 ]
  • [ 6530-09-2 ]
  • [ 110-17-8 ]
  • N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1H-indazole-6-carboxamide fumarate [ No CAS ]
  • 5
  • [ 170487-40-8 ]
  • [ 704-91-6 ]
YieldReaction ConditionsOperation in experiment
Ca. 97% With water; lithium hydroxide; In tetrahydrofuran; methanol; at 20℃; for 16h; To a stirred solution of compound methyl lH-indazole-6-carboxylate (1.0 g, 5.676 mmol, leq) in tetrahydrofuran/rnethanol/H20 (1:1:1; lOmL) was added LIOH (476 mg, 11.353 mmol, 2 eq) at room temperature then stirred for 16h. The solvents were evaporated, residue diluted with water (lOmL) andacidified with 2N HCI (pH4-5) to get solid precipitate, filtered and dried to get compound 2 (900 mg,?97percent) as off white solid. TLC system: methanol/dichloromethane (1:9), Rf: 0.1.?H NMR (300 MHz, DMSO-d6): oe 13,36 (s, 1H), 13.04 (s, lH), 8.24?8.08 (m, 2H), 7.85 (dd, J 8.5, 0.9 Hz, I H), 7.67 (dd, J = 8.4, 1.3 Hz, I H).
87% With lithium hydroxide; water; In tetrahydrofuran; at 50℃; for 4h; b) A solution of compound 26e2 (5.0 g, 28.4 mmol) in THF (56 mL) was treated with LiOH (21 mL of a 2M aqueous solution, 42 mmol), and the reaction mixture is stirred at 50 °C. After 4 hours, the reaction mixture was cooled to room temperature and diluted with water. The basic aqueous layer was rinsed with diethyl ether, acidified to pH 3-4 by the addition of 1 M HCI, and extracted with ethyl acetate. The aqueous layer was extracted further with ethyl acetate, and the combined organic layers were rinsed with brine, dried over MgS04, and concentrated to afford 4.0 g (87percent yield) of compound 26. 3.'H NMR (CD30D) 8 7.79-7. 87 (m, 2H), 8.14 (s, 1H), 8.29 (s, 1H) ; ES (+) MS m/e = 163 (M+1).
85.6% With water; lithium hydroxide; In tetrahydrofuran; at 50℃; for 4h; A mixture of intermediate (12) (44.0g, 0.25mol) was dissolved in tetrahydrofuran (a 500 mL) was added 2NLiOH aqueous solution (200mL, 0.40mol), the reaction was stirred at 50 4h. Cooling to room temperature, the tetrahydrofuran was evaporated under reduced pressure, the residue was added distilled water (200 mL), washed with 1NHCl acidified to pH 3.5, added with ethyl acetate (3 × 500mL) extraction, the combined organic layer was washed with brine (a 500 mL), no over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give a pale yellow solid intermediate (13) 34.7g, yield 85.6percent.
85.6% With water; lithium hydroxide; In tetrahydrofuran; at 50℃; for 4h; Intermediate (12) (44.0 g, 0.25 mol) was dissolved in tetrahydrofuran (500 mL), and an aqueous solution of 2N LiOH (200 mL, 0.40 mol) was added. The reaction mixture was stirred at 50°C for 4 h, and was then cooled to roomtemperature. Tetrahydrofuran was distilled off under reduced pressure, and the residue was diluted by adding distilledwater (200 mL). The resulting mixture was acidified to pH 3.5 with 1 N HCl, and was extracted with ethyl acetate (33500mL). The combined organic layer was washed with brine (500 mL), dried over anhydrous sodium sulfate, and filtered.The filtrate was concentrated under reduced pressure to obtain intermediate (13) as a light yellow solid (34.7 g, yield:85.6percent).MASS (ESI+) m/z = 163 (M+H)+.1 H NMR (400 MHz, CD3OD): 7.79-7.87 (m, 2H), 8.14 (s, 1H), 8.29 (s, 1H).
85.6% With water; lithium hydroxide; In tetrahydrofuran; at 50℃; for 4h; Methyl 1H-indazole-6-carboxylate (44.0 g, 0.25 mol) was dissolved in tetrahydrofuran (500 mL).2N LiOH aqueous solution (200 mL, 0.40 mol) was added.The reaction solution was stirred at 50 ° C for 4 h.After cooling to room temperature, tetrahydrofuran was evaporated under reduced pressure and the residue was diluted with distilled water (200 mL) and acidified to pH 3.5 with 1N HCl.Ethyl acetate (3 × 500 mL) was added for extraction.The mixed organic layer was washed with brine (500 mL).Dry over anhydrous sodium sulfate, filter,The filtrate was concentrated under reduced pressure to give a pale yellowColor solid intermediate (13) 34.7g,The yield was 85.6percent.

  • 6
  • [ 940877-16-7 ]
  • [ 704-91-6 ]
  • [ 940877-88-3 ]
YieldReaction ConditionsOperation in experiment
99% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); for 2h; d) A solution of compound 26. 3 (7.8 g, 20.8 mmol), compound 26. 4 (3. 4 g, 20.8 mmol), 1-hydroxybenzotriazole hydrate ("HOBt", 3.5 g, 22.3 mmol), and diisopropylethylamine ("DIEA", 14 mL, 83.3 mmol) in DMF (100 mL) was treated with EDCI (4.4 g, 22.3 mmol). After 2 h, the reaction mixture was treated with 1 M HC1 and extracted with ethyl acetate. The combined organic extracts were rinsed with NaHC03 (sat'd), rinsed with brine, rinsed with water, dried over MgS04, and concentrated to afford 8.4 g (99percent yield) of the title compound. ES (+) MS m/e = 404 (M+1).
  • 8
  • [ 704-91-6 ]
  • [ 104224-96-6 ]
  • [ 219507-11-6 ]
YieldReaction ConditionsOperation in experiment
B N2-(4-t-Butylbenzoyl)-N1-(6-indazolylcarbonyl)-4-methoxycarbonyl-1,2-benzenediamine By methods substantially equivalent to those described in Example 9-C, N2-(4-t-butylbenzoyl)-N1-(6-indazolylcarbonyl)-4-methoxycarbonyl-1,2-benzenediamine (0.1 g, 5percent) was prepared from 4-methoxycarbonyl-N2-(4-t-butylbenzoyl)-1,2-benzenediamine and <strong>[704-91-6]6-indazolecarboxylic acid</strong>. 1H NMR FD-MS, m/e 438.3 (M+) Anal. for C26H22N4O3: Calc: C, 68.92; H, 5.57; N, 11.91. Found: C, 68.94; H, 5.62; N, 11.79.
  • 9
  • [ 704-91-6 ]
  • [ 219492-28-1 ]
  • [ 219507-07-0 ]
YieldReaction ConditionsOperation in experiment
330 mg (26%) With 1,2-dichloro-ethane; In methanol; ethyl acetate; N,N-dimethyl-formamide; C N2-(4-t-Butylbenzoyl)-N1-(6-indazolylcarbonyl)-1,2-benzenediamine To a stirring solution of N2-(4-t-butylbenzoyl)-1,2-benzenediamine (830 mg, 3.1 mmol) and <strong>[704-91-6]6-indazolecarboxylic acid</strong> (European Pat. Appln. Pub. No. 242 167 A2, p 43) (500 mg, 3.1 mmol) in DMF (5 mL) was added EDC (1.19 g, 6.2 mmol). After 12 h, the solvent was removed in vacuo and the residue was dissolved in ethyl acetate and washed twice with water and twice with brine. The organic phase was dried with MgSO4, filtered and concentrated in vacuo, then chromatographed over silica gel, eluding with a solvent gradient of dichloromethane through 5percent methanol/dichloromethane. The product containing fractions were combined and concentrated in vacuo to give 330 mg (26percent) of an off-white solid. 1H NMR FD-MS, m/e 412 (M+) Anal. for C24H24N4O2: Calc: C, 72.80; H, 5.87; N, 13.58. Found: C, 72.15; H, 5.80; N, 13.19.
  • 10
  • [ 704-91-6 ]
  • [ 74-89-5 ]
  • [ 906000-49-5 ]
YieldReaction ConditionsOperation in experiment
99% With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide; at 0 - 20℃; General procedure: A DMF solution of 3-(5-amino-1H-indazol-3-yl)benzenesulfonamide 2,2,2-trifluoroacetate (1.0equiv), DIPEA (N,N-diisopropylethylamine, 3equiv) and RCO2H (1.05equiv) at 0°C was treated with TBTU (O-(Benzotriazol-1-yl)-N,N,N?,N?-tetramethyluronium tetrafluoroborate) (1.05equiv) added in one portion. The reaction was stirred allowing slowly to warm to rt. After several hours or overnight stirring the crude reaction was purified directly by preparative HPLC. Alternatively, a DMF solution of 3-(3-sulfamoylphenyl)-1H-indazole-5-carboxylic acid (1.0equiv), DIPEA (3equiv) and RR?NH (1.05equiv) at 0°C or rt was treated with TBTU (1.05equiv) added in one portion. The reaction was stirred allowing slowly to warm to rt. After several hours or overnight stirring the crude reaction was purified directly by prepHPLC.
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; at 23℃; for 14h; A mixture of <strong>[704-91-6]1H-<strong>[704-91-6]indazole-6-carboxylic acid</strong></strong> (4-1, 1.11 g, 6.85 mmol, 1 equiv), N,N- diisopropylethylamine (2.65 g, 20.5 mmol, 3.00 equiv), (1H-l,2,3-benzotriazol-1-yloxy)(tripyrrolidin-1- yl)rhohosphonium hexafluorophosphate (Pybop, 5.34 g, 10.3 mmol, 1.50 equiv) and methylamine (10.3 mL (2M in THF), 20.5 mmol, 3 .00 equiv) in DMF (10 mL) was stirred at 23 °C for 14 h. The reaction mixture was partitioned between a 1: 1 aqueous mixture of of sodium chloride solution and sodium bicarbonate solution and ethyl acetate (2 x 50 mL). The aqueous layer was then acidified to pH 5 and washed with ethyl acetate (2 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (hexanes initially, grading to EPO <DP n="64"/>100percent EtOAc, then 10percent MeOH in EtOAc) to give N-methyl-1H-indazole-6-carboxamide (4-2) as a light brown solid. LRMS m/z (M+H) 176.2 found, 176.1 required.
  • 11
  • [ 141290-59-7 ]
  • [ 704-91-6 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; water; In ethanol; at 80℃; for 4h; A mixture of 1H-indazole-6-carbonitrile (1-3, 1.50 g, 10.5 mmol, 1.00 equiv), and sodium hydroxide ( 1.26 g, 31.4 mmol, 3 equiv) in a 1 : 1 mixture of ethanol and IN aqueous sodium hydroxide (5 mL) was heated to 80 °C for 4 h. The reaction mixture was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate (4 x 50 mL). The organic layer was discarded and the aqueous layer was acidified to pH 5 and washed with ethyl acetate (2 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated to give 1H-indazole-6-carboxylic acid (4- 1) as an off-white solid. The LRMS m/z (M+H ) 163.1 found, 163.0 required.
With sodium hydroxide; In ethanol; water; at 80℃; for 4h; A mixture of lH-indazole-6-carbonitrile (1-3, 1.50 g, 10.5 mmol, 1.00 equiv), and sodium hydroxide (1.26 g, 31.4 mmol, 3 equiv) in a 1:1 mixture of ethanol and IN aqueous sodium hydroxide (5 mL) was heated to 80 0C for 4 h. The reaction mixture was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate (4 x 50 mL). The organic layer was discarded and the aqueous layer was acidified to pH 5 and washed with ethyl acetate (2 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated to give lH-indazole-6-carboxylic acid (4-1) as an off-white solid. The LRMS m/z (M+H ) 163.1 found, 163.0 required.
  • 12
  • [ 704-91-6 ]
  • 3-bromo-1H-indazole-6-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With bromine; sodium hydrogensulfite; In acetic acid; (b) To a solution of 6-carboxyindazole (4.0 g) in acetic acid (140 ml) was added bromine (1.53 ml), and the mixture was stirred in the dark for 24 hours. After the addition of saturated sodium bisulfite (50 ml) and brine (100 ml), the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated. The resulting solid was powdered and vacuum dried to afford 3-bromo-6-carboxyindazole as a light brown solid (5.88 g, 99percent), mp >250°.
99% With bromine; sodium hydrogensulfite; In acetic acid; (b) To a solution of 6-carboxyindazole (4.0 g) in acetic acid (140 ml) was added bromine (1.53 ml), and the mixture was stirred in the dark for 24 hours. After the addition of saturated sodium bisulfite (50 ml) and brine (100 ml), the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated. The resulting solid was powdered and vacuum dried to afford 3-bromo-6-carboxyindazole as a light brown solid (5.88 g, 99percent), mp >250°.
With bromine; acetic acid; at 25℃; for 16h;in the dark; Bromine (0.385 mL, 7.48 mmol) was added dropwise to a solution of 1 H-<strong>[704-91-6]indazole-6-carboxylic acid</strong> (1 g, 5.98 mmol) in acetic acid (30 mL) and the reaction mixture was stirred for 16 h at 25°C in the dark. The reaction was quenched by addition of a saturated aqueous solution of Na2S03 (12 mL) and brine (25 mL) and extracted with EtOAc (x3). The combined organic extracts were washed with brine, dried (Na2S04), filtered and concentrated. The material thus obtained was used without further purification in the next step. MS (UPLC/MS): 239.1/241.1 [M-H]-, 481.3/483.3 [2M-H]-; tR (UPLC conditions f): 1.59 min.
  • 13
  • [ 540-80-7 ]
  • ethereal HCl [ No CAS ]
  • [ 2458-12-0 ]
  • [ 704-91-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; potassium acetate; trifluoroborane diethyl ether; In tetrahydrofuran; chloroform; ethyl acetate; acetone; (a) To a solution of boron trifluoride etherate (18 ml) in chloroform (450 ml, Al2 O3 treated) at -15° was added a solution of 3-amino-4-methylbenzoic acid (15.1 g) in tetrahydrofuran (150 ml) over 15 minutes and the resulting mixture was then stirred for an additional 5 minutes. To this mixture was added t-butyl nitrite (14 ml), and the reaction was warmed to 5°. After stirring for 1 hour, potassium acetate (49 g) and 18-crown-6 (2.65 g) were added. The reaction mixture was allowed to warm to room temperature and stirred for 72 hours. The reaction mixture was evaporated, and 3:7 acetone:ethyl acetate (500 ml) and 1N hydrochloric acid (150 ml) were added. After stirring for 2 hours, brine (150 ml) was added to the mixture and the mixture filtered. The aqueous filtrate was extracted with 3:7 acetone:ethyl acetate (2*100 ml). The combined organic extract was dried (MgSO4) and evaporated. The resulting residue was dissolved in hot acetic acid (250 ml) and 250 ml saturated ethereal HCl and 250 ml ether were added sequentially. After cooling to room temperature, the precipitate was filtered and treated with 3:7 acetone:ethyl acetate (500 ml) and brine (100 ml) for 1 hour. After the phases were separated, the aqueous layer was extracted with ethyl acetate (100 ml). The combined organic extracts were washed with brine, dried (MgSO4) and evaporated to afford 6-carboxyindazole as a brown solid (9.8 g, 57percent), mp >250°.
With hydrogenchloride; potassium acetate; trifluoroborane diethyl ether; In tetrahydrofuran; chloroform; ethyl acetate; acetone; (a) To a solution of boron trifluoride etherate (18 ml) in chloroform (450 ml, Al2O3 treated) at -15° was added a solution of 3-amino-4-methylbenzoic acid (15.1 g) in tetrahydrofuran (150 ml) over 15 minutes and the resulting mixture was then stirred for an additional 5 minutes. To this mixture was added t-butyl nitrite (14 ml), and the reaction was warmed to 5°. After stirring for 1 hour, potassium acetate (49 g) and 18-crown-6 (2.65 g) were added. The reaction mixture was allowed to warm to room temperature and stirred for 72 hours. The reaction mixture was evaporated, and 3:7 acetone:ethyl acetate (500 ml) and 1N hydrochloric acid (150 ml) were added. After stirring for 2 hours, brine (150 ml) was added to the mixture and the mixture filtered. The aqueous filtrate was extracted with 3:7 acetone:ethyl acetate (2 x 100 ml). The combined organic extract was dried (MgSO4) and evaporated. The resulting residue was dissolved in hot acetic acid (250 ml) and 250 ml saturated ethereal HCl and 250 ml ether were added sequentially. After cooling to room temperature, the precipitate was filtered and treated with 3:7 acetone:ethyl acetate (500 ml) and brine (100 ml) for 1 hour. After the phases were separated, the aqueous layer was extracted with ethyl acetate (100 ml). The combined organic extracts were washed with brine, dried (MgSO4) and evaporated to afford 6-carboxyindazole as a brown solid (9.8 g, 57percent), mp >250°.
  • 14
  • [ 704-91-6 ]
  • [ 170487-40-8 ]
YieldReaction ConditionsOperation in experiment
6.75 g (82%) With sulfuric acid; In methanol; water; 1.B 1H-Indazole-6-carboxylic acid methyl ester A mixture of 7.59 g (46.8 mmol, 1.0 equiv) <strong>[704-91-6]1H-<strong>[704-91-6]indazole-6-carboxylic acid</strong></strong> in 500 mL CH3OH and 1 mL conc. H2SO4 was heated to reflux for 8 hours, then allowed to stir at room temperature for 18 hours. The mixture was concentrated to ~200 mL, diluted with 1 L ethyl acetate, and washed 1*250 mL saturated aqueous NaHCO3, 1*250 mL H2O, 1*250 mL brine, and dried over Na2SO4. The aqueous washes were extracted with two portions of ethyl acetate to recover additional product. The organic layers were combined, concentrated, and dried to give 6.75 g (82percent) of a yellow-orange-tan solid: 1H NMR (300 MHz, CDCl3) delta 10.8 (br s, 1H), 8.28 (dd, 1H, J=0.9, 1.9 Hz), 8.15 (d, 1H, J=1.0 Hz), 7.8 (m, 2H), 3.97 (s, 3H): MS (Cl, NH3) m/z 177 (M+H+, base).
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