Triethylamine → Tert-butyl N-(4-(1-oxo-1-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methylamino)propan-2-yl)benzyl)sulfamoylcarbamate

HRID 1428795Notes

Reaction equation

HRID 1428795 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:31])[C:10]([NH:12][CH2:13][C:14]2[C:15]([C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=2)=[O:11])=[CH:5][CH:4]=1.[C:32]([O:36][C:37]([NH:39][S:40](N1C=CC(=[N+](C)C)C=C1)(=[O:42])=[O:41])=[O:38])([CH3:35])([CH3:34])[CH3:33].C(N(CC)CC)C>ClCCl>[O:11]=[C:10]([NH:12][CH2:13][C:14]1[C:15]([C:24]2[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)=[N:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=1)[CH:9]([C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH:1][S:40]([NH:39][C:37](=[O:38])[O:36][C:32]([CH3:34])([CH3:33])[CH3:35])(=[O:41])=[O:42])=[CH:8][CH:7]=1)[CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 866802302-(4-(Aminomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamideHCID 178482963HCID 178482963, compound

Product 1

HCID 86680231Tert-butyl N-(4-(1-oxo-1-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methylamino)propan-2-yl)benzyl)sulfamoylcarbamateYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-(4-(aminomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (167 mg, 0.39 mmol) in dichloromethane the intermediate (A) (117 mg, 0.39 mmol) and triethylamine (0.20 mL, 0.56 mmol) was added was stirred for overnight. The reaction mixture was stirred for overnight at room temperature. The mixture was diluted with dichloromethane and washed with water, brine, dried over magnesium sulfate and filtered. The filtrate was evaporated and the residue was purified by column chromatography. Tert-butyl N-(4-(1-oxo-1-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methylamino)propan-2-yl)benzyl)sulfamoylcarbamate (118 mg) was obtained as 50% yield.

Workup

  1. stirringThe reaction mixture was stirred for overnight at room temperature
  2. washwashed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6a5bc5aa6fc141fd8f7d279d4a8ebf36
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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