7-Chloro-6-fluoro-1-methoxyisoquinoline → 1-[3-(7-Chloro-1-methoxyisoquinolin-6-yloxy)-cyclobutyl]-1-(4-fluorophenyl)-propylamine

Reaction equation

N[CH:2]([C:5]1([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)CC(O)[CH2:6]1)[CH2:3]C.ClC1C=C2C(C=C[N:24]=C2OC)=CC=1F.[Cl:31][C:32]1[CH:41]=[C:40]2[C:35]([CH:36]=[CH:37][N:38]=[C:39]2[O:42][CH3:43])=[CH:34][C:33]=1[O:44][CH:45]1[CH2:50]CC(C(N)(C2C=CC(OC)=CC=2)C)C[CH2:46]1>>[Cl:31][C:32]1[CH:41]=[C:40]2[C:35]([CH:36]=[CH:37][N:38]=[C:39]2[O:42][CH3:43])=[CH:34][C:33]=1[O:44][CH:45]1[CH2:50][CH:6]([C:5]([NH2:24])([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH2:2][CH3:3])[CH2:46]1

Participants

Reactant 3

HCID 583808287-Chloro-6-fluoro-1-methoxyisoquinoline

HCID 583809811-[4-(7-Chloro-1-methoxyisoquinolin-6-yloxy)-cyclohexyl]-1-(4-methoxyphenyl)-ethylamine

HCID 583810401-(1-Aminopropyl)-1-(4-fluorophenyl)cyclobutan-3-ol

Product 1

HCID 670756811-[3-(7-Chloro-1-methoxyisoquinolin-6-yloxy)-cyclobutyl]-1-(4-fluorophenyl)-propylamine

Procedure

1-[3-(7-chloro-1-methoxyisoquinolin-6-yloxy)-cyclobutyl]-1-(4-fluorophenyl)-propylamine (2 isomeric mixtures) were prepared from 1-(1-aminopropyl)-1-(4-fluorophenyl)cyclobutan-3-ol (114) and 7-chloro-6-fluoro-1-methoxyisoquinoline (10) as described for (109). The two stereoisomers could be separated by silica gel chromatography, relative stereochemistry was not assigned.