Dimethylamine → N-[1-(Dimethylamino)isoquinolin-5-yl]-N'-[4-(trifluoromethyl)benzyl]urea

HRID 1181452Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[C:7]([NH:12][C:13]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[O:14])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:27][NH:28][CH3:29]>C(O)C>[CH3:27][N:28]([CH3:29])[C:2]1[C:11]2[C:6](=[C:7]([NH:12][C:13]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[O:14])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

N-(1-Chloroisoquinolin-5-yl)-N′-(4-trifluoromethylbenzyl)urea (Example 69; 60 mg) was suspended in ethanol (5 ml). Ethanolic dimethylamine (33%, 2 ml) was added and the mixture heated to 100° C. in a sealed tube for 16 hours after which time TLC indicated complete reaction. The reaction mixture was evaporated and the residue purified by preparative thin layer chromatography (5% methanol-dichloromethane eluant) to give the title compound (20 mg). m/z (ES+) 389 (M+H)+.

Workup

customreaction
customThe reaction mixture was evaporated
customthe residue purified by preparative thin layer chromatography (5% methanol-dichloromethane eluant)

Sources & evidence

ORD record: ord-66b40d54d3c44f59b34300f618bb5d6d
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285563B2

Reaction notes

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