Triethylamine → 2-{3-Methyl-5-[({[6-methyl-4-(trifluoromethyl)pyridin-2-yl]carbamoyl}amino)sulfonyl]-2-thienyl}ethyl acetate

HRID 1696779Notes

Reaction equation

HRID 1696779 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([S:7](=[O:10])(=[O:9])[NH2:8])[S:4][C:3]=1[CH2:11][CH2:12][O:13][C:14](=[O:16])[CH3:15].[C:17]1([O:23]C(Cl)=O)C=CC=CC=1.C(N(CC)CC)C.[CH3:34][C:35]1[N:40]=[C:39]([NH2:41])[CH:38]=[C:37]([C:42]([F:45])([F:44])[F:43])[CH:36]=1>C(#N)C>[C:14]([O:13][CH2:12][CH2:11][C:3]1[S:4][C:5]([S:7]([NH:8][C:17](=[O:23])[NH:41][C:39]2[CH:38]=[C:37]([C:42]([F:45])([F:43])[F:44])[CH:36]=[C:35]([CH3:34])[N:40]=2)(=[O:10])=[O:9])=[CH:6][C:2]=1[CH3:1])(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 184285216-Methyl-4-(trifluoromethyl)pyridin-2-amineHCID 67273589HCID 67273589, compound

Product 1

HCID 426288892-{3-Methyl-5-[({[6-methyl-4-(trifluoromethyl)pyridin-2-yl]carbamoyl}amino)sulfonyl]-2-thienyl}ethyl acetateYield 177.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.235 g acetic acid 2-(3-methyl-5-sulfamoyl-thiophen-2-yl)-ethyl ester in 5 ml acetonitrile was added 0.188 g phenylchloroformate and 0.252 g triethylamine at 0° C. and the mixture was stirred at this temperature for 2 h. To the resulting suspension was added 0.220 g 6-methyl-4-trifluoromethyl-pyridin-2-ylamine and the mixture was heated to 60C for 18 h. The reaction mixture was partitioned between 10% citric acid and ethyl acetate. The phases were separated and the organic phase was washed with brine and evaporated. The residue was triturated with diethylether. The solid was collected by filtration to yield 0.736 g of the title compound as light yellow crystals. MS (ISN) M−H+=463.9

Workup

  1. customThe reaction mixture was partitioned between 10% citric acid and ethyl acetate
  2. customThe phases were separated
  3. washthe organic phase was washed with brine
  4. customevaporated
  5. customThe residue was triturated with diethylether
  6. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-2f25da19c7c44a488f37b7adb7d47f92
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

Loading…