Sodium Bicarbonate → 2-(4-((sulfamoylamino)methyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide

HRID 1428800Notes

Reaction equation

HRID 1428800 reaction equation
[O:1]=[C:2]([NH:24][CH2:25][C:26]1[C:27]([C:36]2[CH:37]=[C:38]([CH3:42])[CH:39]=[CH:40][CH:41]=2)=[N:28][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:31]=1)[CH:3]([C:5]1[CH:23]=[CH:22][C:8]([CH2:9][NH:10][S:11]([NH:14]C(=O)OC(C)(C)C)(=[O:13])=[O:12])=[CH:7][CH:6]=1)[CH3:4].C(=O)(O)[O-].[Na+]>ClCCl>[S:11]([NH:10][CH2:9][C:8]1[CH:22]=[CH:23][C:5]([CH:3]([CH3:4])[C:2]([NH:24][CH2:25][C:26]2[C:27]([C:36]3[CH:37]=[C:38]([CH3:42])[CH:39]=[CH:40][CH:41]=3)=[N:28][C:29]([C:32]([F:33])([F:35])[F:34])=[CH:30][CH:31]=2)=[O:1])=[CH:6][CH:7]=1)(=[O:12])(=[O:13])[NH2:14]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86680231Tert-butyl N-(4-(1-oxo-1-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methylamino)propan-2-yl)benzyl)sulfamoylcarbamate

Product 1

HCID 715393392-(4-((sulfamoylamino)methyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamideYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-(4-(1-oxo-1-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methylamino)propan-2-yl)benzyl)sulfamoylcarbamate (250 mg, 0.412 mmol) in dichloromethane (2 mL) trifluoroacetic acid (0.2 mL) was added at room temperature. The mixture was stirred 12 h at room temperature. The mixture was neutralized by sodium bicarbonate to pH 7-8 and extracted with ethyl acetate and washed with brine. Drying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography gave 2-(4-((sulfamoylamino)methyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (example 88) (138 mg, 66%).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialDrying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography

Sources & evidence

ORD record
ord-0b64de2cd3bc49b28d54d88bc6f7ee57
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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