Hydrochloric Acid → HCID 10027302, compound

HRID 585043Notes

Reaction equation

HRID 585043 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[NH:20][S:21]([C:24]2[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([O:28]C)=[O:27])(=[O:23])=[O:22])=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+].Cl>CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][C:11]=2[NH:20][S:21]([C:24]2[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([OH:28])=[O:27])(=[O:22])=[O:23])=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22339370HCID 22339370, compound

Product 1

HCID 10027302HCID 10027302, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a vial are placed methyl 2-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino}sulfonyl)benzoate (289 mg, 0.608 mmol), 1M NaOH (10 mL), and MeOH (10 mL). The mixture is efficiently shaken at rt for 16 h. 1M HCl is added to adjust the pH to 1. The precipitated was filtered and purified by preparative thin layer chromatography. The yield is 65 mg of 2-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino}sulfonyl)benzoic acid, 23%. 1H NMR (400 MHz, DMSO-d6): □ 10.92 (s, 1 H), 9.98 (s, 1 H), 7.58-7.56 (m, 3 H), 7.44-7.43 (m, 2 H), 7.38-7.30 (m, 3 H), 7.21-7.17 (m, 1 H), 7.02-7.00 (m, 2 H). HRMS for C21H14F3N3O4S 462.0754 (M+H)+.

Workup

  1. filtrationThe precipitated was filtered
  2. custompurified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-0472336398944181ba9649b7d265de23
Source dataset
uspto-grants-2005_08
Patent number
US06930106B2

Reaction notes

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