4-Fluorobenzamide → 1-Cyano-7-(4-fluoro-benzoylamino)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester

HRID 1481169Notes

Reaction equation

HRID 1481169 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:18]#[N:19])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11](Br)[CH:10]=2)=[O:5])[CH3:2].[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=[O:26])=[CH:23][CH:22]=1>>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:18]#[N:19])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([NH:27][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][C:21]([F:20])=[CH:22][CH:23]=1)[CH:10]=2)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 715724-FluorobenzamideHCID 898128697-Bromo-1-cyano-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester

Product 1

HCID 898131841-Cyano-7-(4-fluoro-benzoylamino)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester

Procedure

1-Cyano-7-(4-fluoro-benzoylamino)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester was prepared from 7-Bromo-1-cyano-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester under conditions analogous to Example 116(a) using 4-fluorobenzamide. 1H NMR (200 MHz, DMSO): δ ppm=10.85 (s, 1H), 8.83 (s, 1H), 8.39 (m, 2H), 8.11 (m, 2H), 7.37 (m, 3H) 4.49 (q, 2H), 1.41 (t, 3H.)

Sources & evidence

ORD record
ord-7ca0c864605c4f60b59feb6fe7b1b31d
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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