Hydrochloric Acid → 3-(2-Chloro-4-isopropyl-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid

HRID 2264988Notes

Reaction equation

HRID 2264988 reaction equation
C([O:3][C:4]([C:6]1[N:14]([CH3:15])[C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][C:18]=1[Cl:26])=[O:5])C.[OH-].[Na+].Cl>>[Cl:26][C:18]1[CH:19]=[C:20]([CH:23]([CH3:25])[CH3:24])[CH:21]=[CH:22][C:17]=1[NH:16][C:7]1[C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[N:14]([CH3:15])[C:6]=1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 595965143-(2-Chloro-4-isopropyl-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 595965523-(2-Chloro-4-isopropyl-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acidYield 103.2%

Procedure

A solution of 3-(2-chloro-4-isopropyl-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (230 mg, 0.62 mmol) and 1M NaOH (0.74 ml, 7.4 mmol) in IMS (5 ml) was heated at 60° C. for 3 hours. The reaction mixture was cooled to ambient temperature then acidified to pH 5 using 1M HCl. The fine yellow suspension was filtered to provide the title compound as a yellow solid (220 mg, 100%). LCMS (method B): RT=2.53 min, M+H+=344.

Workup

  1. filtrationThe fine yellow suspension was filtered

Sources & evidence

ORD record
ord-43c945ae9b97448895d5ccce819c6fd4
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

Loading…