Cyclohexylurea → 7-(3-Cyclohexyl-ureido)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester

HRID 1481155Notes

Reaction equation

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

Participants

Reactant 2

HCID 69684Cyclohexylurea

HCID 89813095Ethyl 7-bromo-4-hydroxyisoquinoline-3-carboxylate

Product 1

HCID 898128727-(3-Cyclohexyl-ureido)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester

Procedure

7-(3-Cyclohexyl-ureido)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester was prepared from 7-Bromo-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester under conditions analogous to Example 116(a) using cyclohexyl urea. 1H NMR (200 MHz, CDCl3): δ ppm=11.79 (br s, 1H), 8.66 (s, 1H), 8.20 (m, 2H), 7.67 (br s, 1H), 7.50 (d, 1H), 5.30 (d, 1H), 4.53 (q, 2H), 3.71-3.63 (m, 1H), 1.98 (br d, 2H), 1.68-1.07 (m, 19H.)

Sources & evidence

ORD record: ord-634887c707524e16aceb9b5e60b23438
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409892B2

Reaction notes

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