Water → Glycine, N-[(4-chloro-1H-pyrrolo[2,3-B]pyridin-5-YL)carbonyl]-, methyl ester

HRID 1360182Notes

Reaction equation

HRID 1360182 reaction equation
[Cl:1][C:2]1[C:7]([C:8](N2C=CN=C2)=[O:9])=[CH:6][N:5]=[C:4]2[NH:15][CH:16]=[CH:17][C:3]=12.C(N(C(C)C)C(C)C)C.Cl.[CH3:28][O:29][C:30](=[O:33])[CH2:31][NH2:32].O>CN(C)C=O>[Cl:1][C:2]1[C:7]([C:8]([NH:32][CH2:31][C:30]([O:29][CH3:28])=[O:33])=[O:9])=[CH:6][N:5]=[C:4]2[NH:15][CH:16]=[CH:17][C:3]=12

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 57928321Methanone, (4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-imidazol-1-yl-

Product 1

HCID 57928282Glycine, N-[(4-chloro-1H-pyrrolo[2,3-B]pyridin-5-YL)carbonyl]-, methyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-chloro-5-(1H-imidazol-1-ylcarbonyl)-1H-pyrrolo[2,3-b]pyridine(300 mg) in N,N-dimethylformamide (3 ml) were added N-ethyl-N-isopropylpropane-2-amine (0.64 ml) and glycine methylester hydrochloride (305 mg) at ambient temperature. The mixture was warmed immediately to 60° C. and stirred at 60° C. for 2 hours. After to the reaction solution was added water, the mixture was stirred for 1 hour. The precipitated solid was filtered, washed with water, and dried to obtain methyl N-[(4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)carbonyl]glycinate (267 mg) as a white solid.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. filtrationThe precipitated solid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-876c1a8a32a545988fe134f65b0093d8
Source dataset
uspto-grants-2011_02
Patent number
US07879844B2

Reaction notes

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