Triethylamine → N-(2-Oxo-2-phenylethyl)-5-(fluoroacetyl)thiophene-2-carboxamide

HRID 1715354Notes

Reaction equation

HRID 1715354 reaction equation
F[C:2]([F:14])(F)[C:3]([C:5]1[S:9][C:8]([C:10]([OH:12])=O)=[CH:7][CH:6]=1)=[O:4].N=C=N.Cl.[NH2:19][CH2:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22].CCN(CC)CC>C(Cl)Cl>[O:22]=[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:20][NH:19][C:10]([C:8]1[S:9][C:5]([C:3](=[O:4])[CH2:2][F:14])=[CH:6][CH:7]=1)=[O:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 160435CarbodiimideHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 242747015-(2,2,2-Trifluoroacetyl)thiophene-2-carboxylic acid

Product 1

HCID 86628838N-(2-Oxo-2-phenylethyl)-5-(fluoroacetyl)thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Example 1, A1 in DCM was added Pol-supported carbodiimide (2 eq) and the suspension was stirred at RT for 30 min. A solution of 2-aminoacetophenone HCl (1.1 eq) and Et3N (1.1 eq) in DCM was added and the resulting suspension was stirred at RT overnight. The resin was filtered, washed with DCM, and the filtrate was evaporated at reduced pressure. Purification by flash chromatography on silica gel eluting with DCM gave the title compound as a solid.

Workup

  1. stirringthe resulting suspension was stirred at RT overnight
  2. filtrationThe resin was filtered
  3. washwashed with DCM
  4. customthe filtrate was evaporated at reduced pressure
  5. customPurification by flash chromatography on silica gel eluting with DCM

Sources & evidence

ORD record
ord-8ee931b835914bd4a9f23d64613a623f
Source dataset
uspto-grants-2010_09
Patent number
US07799825B2

Reaction notes

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