Triethylamine → Methyl 6-[({[5-(2-acetoxyethyl)-4-methyl-2-thienyl]sulfonyl}carbamoyl)amino]-4-(trifluoromethyl)pyridine-2-carboxylate

HRID 1696770Notes

Reaction equation

HRID 1696770 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][O:35][C:36]([C:38]1[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=[C:40]([NH2:48])[N:39]=1)=[O:37]>C(#N)C>[CH3:34][O:35][C:36]([C:38]1[CH:43]=[C:42]([C:44]([F:47])([F:45])[F:46])[CH:41]=[C:40]([NH:48][C:17](=[O:23])[NH:8][S:7]([C:5]2[S:4][C:3]([CH2:11][CH2:12][O:13][C:14](=[O:16])[CH3:15])=[C:2]([CH3:1])[CH:6]=2)(=[O:10])=[O:9])[N:39]=1)=[O:37]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 67273589HCID 67273589, compoundHCID 67274099Methyl 6-amino-4-(trifluoromethyl)picolinate

Product 1

HCID 42630611Methyl 6-[({[5-(2-acetoxyethyl)-4-methyl-2-thienyl]sulfonyl}carbamoyl)amino]-4-(trifluoromethyl)pyridine-2-carboxylateYield 73.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 0.263 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 ° C. and the mixture was stirred at this temperature for 2 h. To the resulting suspension was added 0.220 g 6-amino-4-trifluoromethyl-pyridine-2-carboxylic acid methyl ester and the mixture was heated to 60° C. 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 t-butylmethylether. The solid was collected by filtration to yield 0.376 g of the title compound as white crystals. MS (ISN) M−H+=508.3

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 t-butylmethylether
  6. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-d1ffab1877b14f14bb6765dcfebf2b90
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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