4-Aminoquinoline → 6-[cyclohexyl(methyl)amino]-N-quinolin-4-ylpyrimidine-4-carboxamide

HRID 1746724Notes

Reaction equation

HRID 1746724 reaction equation
[CH:1]1([N:7]([CH3:17])[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([OH:16])=O)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=[CH:21][CH:20]=1>>[CH:1]1([N:7]([CH3:17])[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[O:16])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 684764-AminoquinolineHCID 594470776-[Cyclohexyl(methyl)amino]pyrimidine-4-carboxylic acid2×

Product 1

HCID 251827776-[cyclohexyl(methyl)amino]-N-quinolin-4-ylpyrimidine-4-carboxamide

Procedure

Following the general method as outlined in Example 1, starting from 6-[cyclohexyl(methyl)amino]pyrimidine-4-carboxylic acid (Intermediate 10) and 4-aminoquinoline (Tyger), the title compound was obtained as an off-white solid after purification by column chromatography (silica) eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-5dc56374b264448284be95bac6cdd56d
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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