Hydrochloric Acid → HCID 57731641, compound

HRID 2234647Notes

Reaction equation

HRID 2234647 reaction equation
C[O:2][C:3](=[O:39])[C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[C:12]3[C:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[O:25][CH3:26])=[CH:17][N:16](S(C4C=CC(C)=CC=4)(=O)=O)[C:13]3=[N:14][CH:15]=2)[CH:7]=[C:6]([Cl:37])[C:5]=1[OH:38].[OH-].[Na+].Cl>C(O)C>[Cl:37][C:6]1[C:5]([OH:38])=[C:4]([CH:9]=[C:8]([C:10]2[CH:11]=[C:12]3[C:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[O:25][CH3:26])=[CH:17][NH:16][C:13]3=[N:14][CH:15]=2)[CH:7]=1)[C:3]([OH:39])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57731630HCID 57731630, compound

Product 1

HCID 57731641HCID 57731641, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

320 mg (0.57 mmol) of 3-chloro-2-hydroxy-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzoic acid methyl ester was dissolved in 20 mL of hot ethanol. 5 mL (14 mmol) of 7 M aqueous sodium hydroxide was added and the mixture was left at ambient temperature for 15 h. The resulting solution was acidified to pH 1 by addition of concentrated aqueous hydrochloric acid. The resulting precipitate was filtered off and dried by suction to afford 232 mg (0.59 mmol, 103%) of 3-chloro-2-hydroxy-5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzoic acid as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.45 (d, 1H), 8.21 (d, 1H), 8.11 (d, 1H), 8.03 (d, 1H), 7.77 (d, 1H), 7.62 (dd, 1H), 7.31 (t, 1H), 7.15 (d, 1H), 7.07 (t, 1H), 3.83 (s, 3H). MS: m/z 395.0 (M+H+).

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. customdried by suction

Sources & evidence

ORD record
ord-ab843aba3c5749f6b47413906a47a8d8
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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