4-Methoxybenzaldehyde → Methyl 2-fluoro-5-({[4-(methyloxy)phenyl]methyl}amino)-3-(2-oxo-1-pyrrolidinyl)benzoate

HRID 852588Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[C:5]([F:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1>>[F:12][C:5]1[C:4]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])=[CH:3][C:2]([NH:1][CH2:25][C:24]2[CH:27]=[CH:28][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

Reactant 2

HCID 312444-Methoxybenzaldehyde

HCID 69357536Methyl 5-amino-2-fluoro-3-(2-oxo-1-pyrrolidinyl)benzoate

Product 1

HCID 69361588Methyl 2-fluoro-5-({[4-(methyloxy)phenyl]methyl}amino)-3-(2-oxo-1-pyrrolidinyl)benzoate

Procedure

Methyl 2-fluoro-5-({[4-(methyloxy)phenyl]methyl}amino)-3-(2-oxo-1-pyrrolidinyl)benzoate (D154) was prepared from methyl 5-amino-2-fluoro-3-(2-oxo-1-pyrrolidinyl)benzoate (D150) in an analogous manner to the process described for Ester 35 (B35) using 4-(methyloxy)benzaldehyde instead of propionaldehyde. [M+H]+=373.4, RT=2.85 min.

Sources & evidence

ORD record: ord-03584a8fa5d243ed8a6cf1267fb2e367
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253198B2

Reaction notes

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