Dimethylformamide dimethyl acetal → 2-(5-(3-Chloro-2-fluorobenzyl)-2-fluoro-4-methoxybenzoyl)-3-dimethylaminoacrylic acid ethyl ester

HRID 391244Notes

Reaction equation

HRID 391244 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]([C:8]1[CH:13]=[C:12]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=2[F:22])[C:11]([O:23][CH3:24])=[CH:10][C:9]=1[F:25])=[O:7])[CH3:2].CO[CH:29](OC)[N:30]([CH3:32])[CH3:31]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:26])[C:5]([C:6](=[O:7])[C:8]1[CH:13]=[C:12]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=2[F:22])[C:11]([O:23][CH3:24])=[CH:10][C:9]=1[F:25])=[CH:29][N:30]([CH3:32])[CH3:31])[CH3:2]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 575728593-(5-(3-Chloro-2-fluorobenzyl)-2-fluoro-4-methoxyphenyl)-3-oxopropionic acid ethyl ester

Product 1

HCID 689553422-(5-(3-Chloro-2-fluorobenzyl)-2-fluoro-4-methoxybenzoyl)-3-dimethylaminoacrylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 3-(5-(3-chloro-2-fluorobenzyl)-2-fluoro-4-methoxyphenyl)-3-oxopropionic acid ethyl ester prepared in Step VI-2 in toluene was added dropwise at 75-85° C., N,N-dimethylformamide dimethyl acetal (5.08 g) with stirring, and the mixture was stirred for 3 hr. After cooling, a solution of 2-(5-(3-chloro-2-fluorobenzyl)-2-fluoro-4-methoxybenzoyl)-3-dimethylaminoacrylic acid ethyl ester in toluene was obtained. This was identified as the title compound by HPLC.

Workup

  1. temperatureAfter cooling

Sources & evidence

ORD record
ord-d617d8bc443e4d3c82e6c4fb3eafa5e4
Source dataset
uspto-grants-2013_02
Patent number
US08383819B2

Reaction notes

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