HCID 178471895, compound → ethyl 2-[2-amino-5-(difluoromethoxy)-3,4,6-trifluorobenzoyl]-3-(cyclopropylamino)prop-2-enoate

HRID 1461032Notes

Reaction equation

HRID 1461032 reaction equation
[CH:1]1([NH:4][CH:5]=[C:6]([C:12](=[O:29])[C:13]2[C:18]([N+:19]([O-])=O)=[C:17]([F:22])[C:16]([F:23])=[C:15]([O:24][CH:25]([F:27])[F:26])[C:14]=2[F:28])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1>C(O)C>[CH:1]1([NH:4][CH:5]=[C:6]([C:12](=[O:29])[C:13]2[C:18]([NH2:19])=[C:17]([F:22])[C:16]([F:23])=[C:15]([O:24][CH:25]([F:26])[F:27])[C:14]=2[F:28])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 178471895HCID 178471895, compound

Product 1

HCID 178471897ethyl 2-[2-amino-5-(difluoromethoxy)-3,4,6-trifluorobenzoyl]-3-(cyclopropylamino)prop-2-enoateYield 80.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

33.63 g (0.079 mole) of ethyl 3-cyclopropylamino-2-(3-difluoromethoxy-2,4,5-trifluoro-6-nitrobenzoyl)acrylate [(XIXa): X=X'=F, R1 =OCHF2, R17 =C2H5 ] were dissolved in 1300 ml of ethanol with heating. A stream of hydrogen was then bubbled through the solution in the presence of 8.4 g of 5% w/w palladium-on-carbon at room temperature for 40 minutes, whilst stirring. At the end of this time, the reaction mixture was filtered, and the filtrate was concentrated by evaporation under reduced pressure. The resulting residue was then purified by silica gel column chromatography using a 9:1 by volume mixture of toluene and ethyl acetate as the eluent, to give 25.1 g of ethyl 3-cyclopropylamino-2-(6-amino-3-difluoromethoxy-2,4,5-trifluorobenzoyl)acrylate [(XIXb): X=X'=F, R1 =OCHF2, R17 =C2H5 ] as a pale yellow powder, melting at 103°-104° C.

Workup

  1. temperaturewith heating
  2. customA stream of hydrogen was then bubbled through the solution in the presence of 8.4 g of 5% w/w palladium-on-carbon at room temperature for 40 minutes
  3. filtrationAt the end of this time, the reaction mixture was filtered
  4. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  5. customThe resulting residue was then purified by silica gel column chromatography
  6. additionby volume mixture of toluene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-cde91cd436284f6eb7edf689d4d4bd9e
Source dataset
uspto-grants-1991_12
Patent number
US05073556

Reaction notes

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