Hydrochloric Acid → 4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-benzoic acid

HRID 2235164Notes

Reaction equation

HRID 2235164 reaction equation
C([O:3][C:4](=[O:35])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:22]=[C:21]3[C:17]([CH:18]=[CH:19][N:20]3[S:23]([C:26]3[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=3[O:33][CH3:34])(=[O:25])=[O:24])=[CH:16][CH:15]=2)=[O:13])=[CH:7][CH:6]=1)C.[Li+].[OH-].Cl>O1CCCC1.CO.O>[Cl:32][C:30]1[CH:29]=[CH:28][C:27]([O:33][CH3:34])=[C:26]([S:23]([N:20]2[C:21]3[C:17](=[CH:16][CH:15]=[C:14]([C:12]([NH:11][C:8]4[CH:9]=[CH:10][C:5]([C:4]([OH:35])=[O:3])=[CH:6][CH:7]=4)=[O:13])[CH:22]=3)[CH:18]=[CH:19]2)(=[O:25])=[O:24])[CH:31]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 588317454-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-benzoic acid ethyl ester

Product 1

HCID 160508144-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-benzoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-benzoic acid ethyl ester (70 mg, 0.14 mmol) in tetrahydrofuran (1.5 ml) and methanol (0.5 ml) was treated with a 1N solution of LiOH in water (0.5 ml). The mixture was stirred at room temperature for 4 hours, then acidified with 1N HCl (0.5 ml). Methanol and tetrahydrofuran were evaporated and the residual slurry was extracted three times with ethyl acetate. The combined organic phases were dried with Na2SO4 and evaporated, and the residue purified by flash chromatography (dichloromethane/methanol gradient), to yield 4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-benzoic acid as a light yellow solid, 17 mg (25%). MS (ISP): m/e=483.0 (M−H); δH (300 MHz; d6-DMSO) 12.77 (1H, bs), 10.60 (1H, s), 8.34 (1H, s), 8.08 (1H, d), 7.91-7.97 (6H, m), 7.75-7.80 (2H, m), 7.23 (1H, d), 6.91 (1H, d), 3.70 (3H, s).

Workup

  1. customMethanol and tetrahydrofuran were evaporated
  2. extractionthe residual slurry was extracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried with Na2SO4
  4. customevaporated
  5. customthe residue purified by flash chromatography (dichloromethane/methanol gradient)

Sources & evidence

ORD record
ord-e08451a94a9142e7ab8dc5d783b4b6fb
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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