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[ CAS No. 228244-04-0 ] {[proInfo.proName]}

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Chemical Structure| 228244-04-0
Chemical Structure| 228244-04-0
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Product Details of [ 228244-04-0 ]

CAS No. :228244-04-0 MDL No. :MFCD01861224
Formula : C10H16N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :MDMSZBHMBCNYNO-QMMMGPOBSA-N
M.W : 196.25 Pubchem ID :6951263
Synonyms :

Calculated chemistry of [ 228244-04-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.34
TPSA : 53.33 ?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) : -6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.36
Log Po/w (XLOGP3) : 1.42
Log Po/w (WLOGP) : 1.53
Log Po/w (MLOGP) : 0.76
Log Po/w (SILICOS-IT) : 0.77
Consensus Log Po/w : 1.37

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.75
Solubility : 3.46 mg/ml ; 0.0176 mol/l
Class : Very soluble
Log S (Ali) : -2.14
Solubility : 1.41 mg/ml ; 0.00717 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.08
Solubility : 16.1 mg/ml ; 0.0822 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.63

Safety of [ 228244-04-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P280-P337+P313-P302+P352+P312-P304+P340+P312 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 228244-04-0 ]

* 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 [ 228244-04-0 ]

[ 228244-04-0 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 67-56-1 ]
  • [ 228244-04-0 ]
  • (2S)-N-(tert-butoxycarbonyl)pyrrolidine-2-carboximidic acid methyl ester [ No CAS ]
  • 2
  • [ 76-05-1 ]
  • [ 228244-04-0 ]
  • (S)-pyrrolidine-2-carbonitrile trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 0℃; for 2.33333h;Inert atmosphere; Boc-2(S)-cyanopyrrolidine was synthesized according to a literature procedure [39]. TFA (20mL, 260mmol) was added dropwise to a solution of Boc-2(S)-cyanopyrrolidine (0.99g, 5.0mmol) in DCM (60mL) under argon at 0C. After 2h 20min the solvent was evaporated yielding the TFA salt of 2(S)-cyanopyrrolidine, which was used directly in the reaction below.
  • 3
  • [ 35150-07-3 ]
  • [ 228244-04-0 ]
YieldReaction ConditionsOperation in experiment
76% With 1,3,5-trichloro-2,4,6-triazine; In N,N-dimethyl-formamide; at 20℃; for 1h; General procedure: A mixture of compound 2 (5 g, 23.3 mmol) and cyanuric chiloride (2.58 g, 14.0 mmol) in DMF (10 mL) was stirred at room temperature for 1 h (monitored by TLC). After the reaction completed, the solution was extracted with EtOAc, washed, dried, concentrated, and purified by flash chromatography on silica gel, eluted with a mixture of PE/EA (1/1, v/v), to afford 3 (3.48 g, 76%) as a white solid. 1H NMR (300 MHz, CDCl3) delta 4.76 (s, 1H), 3.51 (s, 2H), 2.34-2.31 (m, 1H), 2.17-2.10 (m, 2H), 1.90-1.87 (m, 1H), 1.49 (s, 9H). MS (ESI) m/z 197 [M+H]+.
76% With 1,3,5-trichloro-2,4,6-triazine; In N,N-dimethyl-formamide; at 20℃; for 1h; A mixture of compound 9 (5 g, 23.3 mmol) and cyanuric chiloride (2.58 g, 14.0 mmol) in DMF (10 mL) was stirred at roomtemperature for 1 h (monitored by TLC). After the reaction completed, thesolution was extracted with EtOAc, washed, dried, concentrated, and purified byflash chromatography on silica gel, eluted with a mixture of PE/EA (1/1, v/v)to afford 10 (3.48 g, 76%) as a white solid. 1H NMR (CDCl3,300 MHz): delta4.76(s, 1H), 3.51 (s, 2H), 2.34-2.31 (m, 1H), 2.17-2.10 (m, 2H), 1.90-1.87 (m, 1H),1.49 (s, 9H). MS (ESI) m/z 197[M+H]+.
With 1,3,5-trichloro-2,4,6-triazine; N,N-dimethyl-formamide; In dichloromethane; at 20 - 40℃;Inert atmosphere; Dichloromethane (500 ml), L-Prolinamide (100 g), potassium carbonate (60.50 g) were mixed and stirred under nitrogen atmosphere in round bottom flask The reaction mass was cooled to 10-15C and then Di-tert-butyl dicarbonate (210.30 g) was added. Reaction mixture was stirred till completion of the reaction. After completion water (500m1) was added and product was extracted in dichloromethane. Dichloro methane was removed and then dimethyl formamide (140 ml) and dichloromethane (700 ml) were added under nitrogen atmosphere. Cyanuric chloride (72.70 g) was charged in 2-3 equal lots to the reaction mass at 20-25C under nitrogen atmosphere. The reaction mass was maintained at 35-40C for 4-5 hrs. After completion of the reaction solid was filtered and washed with MDC. Methane sulfonic acid (252.60 g) was added to the filtrate and heated the reaction mass to 40-45C for 3-4 hrs. After completion of the reaction the reaction mass was cooled at 0-5C and Triethyl amine (88.65 g) and Chloroacetyl chloride (118.70 g) were added. The reaction mass was maintained at 20-30C for 1-2 hrs under nitrogen atmosphere. After completion of the reaction water was charged and product was extracted in dichloromethane. Organic layer was washed first with dilute HC1 solution and then with ammonia solution. Organic solvent was removed and product was crystallized using isopropyl alcohol. Yield: 75.0gm
55 g With triethylamine; trifluoroacetic anhydride; In dichloromethane; at -15℃; for 3h; step 1:The first reaction solution containing the compound represented by Formula II was cooled to -15.0 C., 30.0 g of triethylamine,A dichloromethane solution containing 0.357 mol of trifluoroacetic anhydride (TFAA) was added dropwise,Dropping time 2h, after the addition was completed, incubated for 1h,Insulation temperature was -15.0 , TLC monitoring showed that the reaction was completed;Step 2: To the solution in Step 1 was added purified water 100mL, washed and stratified;The pH was adjusted to 1 with 1 M hydrochloric acid, the temperature was controlled below 0 C,Stirring for 30-45min, standing stratification;Step 3: The mass concentration of 5% -10% dilute salt water 100mL wash phase;The organic layer was dried over sodium sulfate, filtered and the methylene chloride removed under reduced pressure.55.0 g (0.280 mol) of an oil was obtained as a compound of the formula III.

  • 4
  • [ 228244-04-0 ]
  • [ 681239-91-8 ]
  • 5
  • [ 15761-39-4 ]
  • Fmoc-Glu(tBu)-OHFmoc-Lue-OH [ No CAS ]
  • [ 228244-04-0 ]
  • 6
  • [ 228244-04-0 ]
  • (2'S)-5-<2'-N-(tert-butoxycarbonyl)pyrrolidinyl>-3,6-bis(trifluoromethyl)-1,2,4-triazine [ No CAS ]
  • 7
  • [ 228244-04-0 ]
  • [ 867326-86-1 ]
YieldReaction ConditionsOperation in experiment
With sodium azide; ammonium chloride; In DMF (N,N-dimethyl-formamide); at 93℃; Example 7 (S)-2-(1H-Tetrazol-5-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (A). To a solution of (S)-2-Cyano-pyrrolidine-1-carboxylic acid tert-butyl ester (500 mg, 2.55 mmol) in N,N-dimethyl-formamide (20 mL) is added sodium azide (174 mg, 2.68 mmol) and ammonium chloride (150 mg, 2.81 mmol). The solution is stirred at 93 C. over night. The solution is poured into 5% citric acid solution with ice, and the mixture is extracted with EtOAc. The organic extract is washed with brine, dried and concentrated under vacuum. The crude oil is used directly in the next step without further purification. M+H+=240.
With diethylaluminum azide; In toluene; at 20 - 40℃; for 20 - 30h;Product distribution / selectivity; Example 2: 2-(1 H-Tetrazol-5-yl)pyrrolidine-1- carboxylic acid tert-butyl ester390 mg of granular sodium azide (6mmol) are added at 0 0C to a solution of 2.4 ml of diethyl aluminium chloride (6 mmol, 2.5 molar in toluene) and the mixture is stirred at room temperature for 4 to 7 hours. 981 mg of 2-cyano-pyrrolidine-1 -carboxylic acid t-butyl ester (5 mmol) are added to the diethyl aluminum azide solution at r.t. The mixture is stirred 20 to 30 h at 400C. After complete conversion the mixture is added dropwise to a cold solution (0 0C) of 25 ml of KHSO4 (10%) containing 1.24 g of NaNO2(18 mmol), and extracted four times with 25 ml portion of ethyl acetate. The solvent is removed to give 1.4 g of the crude product which is dissolved again in 20 ml of ethyl acetate. This phase is washed several times with K2CO3 (10%) to extract the product to the aqueous phase as the potassium salt. The basic aqueous phase is carefully treated at 0 0C with KHSO4 solution to pH 5 to avoid the degradation of the Boc-group and the product is then extracted several times with portions of ethyl acetate. The solvent is removed to give the product as a white solid. EPO <DP n="28"/>EI-MS: 238;140 m/z; [g￡ = -75.68 (in MeOH1 c= 0.63); TLC: (Eluent: toluene / etylacetate / acetic acid 20:20:1): Rf= 0.22; |R: s1669 cm"1; s1423 cm"1;m 1372 cm"1; 1160 cm"1; Raman: ml 553cm"1; s1450 cm 1;1H-NMR (500MHz; DMSO): 120C: 1.29 ppm (s, 9H); 1.91 ppm (m, 3H); 2.34 ppm (m, 1 H); 3.49 ppm (m, 2H); 5.1 ppm ( m, 1H);
With diethylaluminum azide; In toluene; xylene; at 0 - 45℃; for 8 - 14h;Product distribution / selectivity; Example 2: 2-(1 H-Tetrazol-5-yl)pyrrolidine-1- carboxylic acid tert-butyl ester390 mg of granular sodium azide (6mmol) are added at 0 0C to a solution of 2.4 ml of diethyl aluminium chloride (6 mmol, 2.5 molar in toluene) and the mixture is stirred at room temperature for 4 to 7 hours. 981 mg of 2-cyano-pyrrolidine-1 -carboxylic acid t-butyl ester (5 mmol) are added to the diethyl aluminum azide solution at r.t. The mixture is stirred 20 to 30 h at 400C. After complete conversion the mixture is added dropwise to a cold solution (0 0C) of 25 ml of KHSO4 (10%) containing 1.24 g of NaNO2(18 mmol), and extracted four times with 25 ml portion of ethyl acetate. The solvent is removed to give 1.4 g of the crude product which is dissolved again in 20 ml of ethyl acetate. This phase is washed several times with K2CO3 (10%) to extract the product to the aqueous phase as the potassium salt. The basic aqueous phase is carefully treated at 0 0C with KHSO4 solution to pH 5 to avoid the degradation of the Boc-group and the product is then extracted several times with portions of ethyl acetate. The solvent is removed to give the product as a white solid. EPO <DP n="28"/>EI-MS: 238;140 m/z; [g￡ = -75.68 (in MeOH1 c= 0.63); TLC: (Eluent: toluene / etylacetate / acetic acid 20:20:1): Rf= 0.22; |R: s1669 cm"1; s1423 cm"1;m 1372 cm"1; 1160 cm"1; Raman: ml 553cm"1; s1450 cm 1;1H-NMR (500MHz; DMSO): 120C: 1.29 ppm (s, 9H); 1.91 ppm (m, 3H); 2.34 ppm (m, 1 H); 3.49 ppm (m, 2H); 5.1 ppm ( m, 1H);
  • 8
  • [ 79-37-8 ]
  • [ 35150-07-3 ]
  • [ 228244-04-0 ]
YieldReaction ConditionsOperation in experiment
66% With pyridine; In ethyl acetate; N,N-dimethyl-formamide; acetonitrile; Preparation 116 tert-butyl (2S)-2-cyano-1-pyrrolidinecarboxylate A solution of oxalyl chloride (11.0 ml, 0.126 mol) and DMF (11.4 ml, 0.138 mol) in MeCN (170 ml) was treated dropwise with a solution of N-Boc-L-proline amide (12.3 g, 0.57mol) and pyridine (20.4 ml, 0.253 mol) in MeCN (30 ml) at 0 C. and stirred at this temperature for 15 minutes. The reaction mixture was diluted with EtOAc and washed with H2O (*3). The organic extract was dried over anhydrous MgSO4 and filtered. The solvent was removed under reduced pressure. The residue was purified on a silica column eluding with a solvent gradient of pentane:EtOAc (80:20) gradually changing to (60:40) to afford the title compound (7.40 g, 66%). 1H nmr: (d6DMSO) 1.40 (9H, s), 1.88 (2H, brs), 2.05-2.30 (2H, m), 3.21 (1H, m), 3.35 (1H, brs), 4.60 (1H, d). MS: 214 (MNH4+)
  • 9
  • [ 104-15-4 ]
  • [ 228244-04-0 ]
  • [ 204387-54-2 ]
YieldReaction ConditionsOperation in experiment
75% In water; acetonitrile; for 24h; General procedure: A solution of compound 3 (10.0 g, 50.96 mmol) in CH3CN (50 mL) was added 4-methylbenzenesulfonic acid hydrate (14.54 g, 76.43 mmol) and stirred at room temperature for 24 h. After the reaction completed, the solution was removed in vacuo. The residual white solid was dissolved in EtOAc (100 mL) and put into fridge overnight, the product 4 (10.3 g, 75%) was precipitated as a white needle crystal. 1H NMR (300 MHz, CD3OD) delta 7.77 (d, J = 7.8 Hz, 2H), 7.20 (d, J = 8.1 Hz, 2H), 4.76-4.75 (m, 1H), 3.51-3.50 (m, 2H), 2.38 (s, 3H), 2.34-2.31 (m, 1H), 2.17-2.09 (m, 2H), 1.90-1.87 (m, 1H). MS (ESI) m/z 97 [M+H]+
75% In acetonitrile; at 20℃; for 24h; A solution of compound 10 (10.0 g, 50.96mmol) in CH3CN (50 mL) was added 4-methylbenzenesulfonic acidhydrate (14.54 g, 76.43mmol) and stirred at room temperature for 24 h. After the reaction completed,the solution was removed in vacuo.The residual white solid was dissolved in EtOAc (100 mL) and put into fridgeovernight, the product 11 (10.3 g, 75%) was precipitated as a white needlecrystal. 1H NMR (CD3OD, 300 MHz): delta 7.77 (d, J = 7.8 Hz, 2H), 7.20 (d, J= 8.1 Hz, 2H), 4.76-4.75 (m, 1H), 3.51-3.50 (m, 2H), 2.38 (s, 3H), 2.34-2.31(m, 1H), 2.17-2.09 (m, 2H), 1.90-1.87 (m, 1H). MS (ESI) m/z 97[M+H]+.
  • 10
  • [ 228244-04-0 ]
  • [ 867326-86-1 ]
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