Hydrochloric Acid → 5-(3-Ethanesulfonyl-phenyl)-3-methyl-9H-pyrido[2,3-b]indole-7-carboxylic acid

HRID 1882243Notes

Reaction equation

HRID 1882243 reaction equation
C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]3[CH:17]=[C:16]([CH3:18])[CH:15]=[N:14][C:10]=3[NH:11]2)=[C:7]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([S:25]([CH2:28][CH3:29])(=[O:27])=[O:26])[CH:20]=2)[CH:6]=1)=[O:4].[OH-].[Na+].Cl>CO>[CH2:28]([S:25]([C:21]1[CH:20]=[C:19]([C:7]2[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:13]=[C:12]3[C:8]=2[C:9]2[CH:17]=[C:16]([CH3:18])[CH:15]=[N:14][C:10]=2[NH:11]3)[CH:24]=[CH:23][CH:22]=1)(=[O:27])=[O:26])[CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 588801605-(3-Ethanesulfonyl-phenyl)-3-methyl-9H-pyrido[2,3-b]indole-7-carboxylic acid methyl ester

Product 1

HCID 588801865-(3-Ethanesulfonyl-phenyl)-3-methyl-9H-pyrido[2,3-b]indole-7-carboxylic acidYield 90.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 132 (260 mg, 0.64 mmol) was stirred 1N NaOH (1 mL) in MeOH (2 mL) at 60° C. for 2 h. The reaction was allowed to cool, and was acidified with 1 N HCl and extracted with CHCl3. Organics were dried (MgSO4) and concentrated to give 228 mg (90%) of the title compound as a white solid. 1H NMR (400 MHz, CD3OD) δ 8.34 (br s, 1H), 8.29 (s, 1H), 8.21 (s, 1H), 8.11 (d, 1H, J=7.6 Hz), 8.01 (d, 1H, J=7.6 Hz), 7.90 (t, 1H, J=7.6 Hz), 7.87 (s, 1H), 7.79 (s, 1H), 3.31 (q, 2H, J=7.2 Hz), 2.35 (s, 3H), 1.29 (t, 3H, J=7.2 Hz). MS (ES) [m+H] calc'd for C21H18N2O4S, 395; found 395.

Workup

  1. temperatureto cool
  2. extractionextracted with CHCl3
  3. dry with materialOrganics were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-74b630be00d04fd7b7351b03b90bf8ca
Source dataset
uspto-grants-2012_11
Patent number
US08318939B2

Reaction notes

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