Sodium Hydroxide → 3-(4-Cyclopropyl-2-fluoro-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid

HRID 2264991Notes

Reaction equation

HRID 2264991 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]2[CH2:25][CH2:24]2)=[CH:19][C:18]=1[F:26])=[O:5])C.[OH-].[Na+]>C(O)(=O)C>[CH:23]1([C:20]2[CH:21]=[CH:22][C:17]([NH:16][C:7]3[C:8]4[CH:9]=[N:10][CH:11]=[CH:12][C:13]=4[N:14]([CH3:15])[C:6]=3[C:4]([OH:5])=[O:3])=[C:18]([F:26])[CH:19]=2)[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59596595HCID 59596595, compound

Product 1

HCID 595964403-(4-Cyclopropyl-2-fluoro-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acidYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-(4-cyclopropyl-2-fluoro-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (197 mg, 0.50 mmol) and 1M NaOH (1.02 ml, 1.02 mmol) in IMS (3 ml) was heated at 60° C. for 2 hours. The reaction mixture was cooled to ambient temperature then acidified to pH 4 using acetic acid. The brown solid was filtered off, the residue dried to provide the title compound (161 mg, 97%). LCMS (method B): RT=2.18 min, M+H+=326.

Workup

  1. filtrationThe brown solid was filtered off
  2. customthe residue dried

Sources & evidence

ORD record
ord-f6a4873bf96b4eb0a9a7f8b286841cc9
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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