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

HRID 45209Notes

Reaction equation

HRID 45209 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

4

Reactant 3

HCID 583808287-Chloro-6-fluoro-1-methoxyisoquinolineHCID 583809811-[4-(7-Chloro-1-methoxyisoquinolin-6-yloxy)-cyclohexyl]-1-(4-methoxyphenyl)-ethylamineHCID 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.

Workup

  1. customThe two stereoisomers could be separated by silica gel chromatography, relative stereochemistry

Sources & evidence

ORD record
ord-12f10541b97c4847839b4de813642ef4
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

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