Hydrochloric Acid → 6-[4-(amino-phenyl-methyl)-cyclohexyloxy]-7-chloro-2H-isoquinolin-1-one

HRID 45217Notes

Reaction equation

HRID 45217 reaction equation
[NH2:1][CH:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH:3]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.[Cl:16][C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[CH:22][N:23]=[C:24]2[O:27]C)=[CH:19][C:18]=1F.Cl>>[NH2:1][CH:2]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH:3]1[CH2:4][CH2:5][CH:6]([O:9][C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][C:17]=2[Cl:16])[C:24](=[O:27])[NH:23][CH:22]=[CH:21]3)[CH2:7][CH2:8]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 583808287-Chloro-6-fluoro-1-methoxyisoquinolineHCID 583809494-(Amino-phenyl-methyl)-cyclohexanol

Product 1

HCID 583809666-[4-(amino-phenyl-methyl)-cyclohexyloxy]-7-chloro-2H-isoquinolin-1-oneYield 11.4%

Procedure

Example 40 was synthesized using the reaction sequence as described for the synthesis of Example 1. 240 mg of 4-(amino-phenyl-methyl)-cyclohexanol (123) and 272 mg of 7-chloro-6-fluoro-1-methoxy-isoquinoline (10) were used to give 51 mg of Example 40 as its hydrochloride. Rt=1.34 min (Method 10). Detected mass: 383.1 (M+H+). 28 mg of the other isomer of 4-(amino-phenyl-methyl)-cyclohexanol (Example 128) were also isolated as its hydrochloride. Rt=1.31 min (Method 10). Detected mass: 383.1 (M+H+). Separation of the two isomers was accomplished by silica gel chromatography after coupling of aminoalcohol 123 and 10. Relative stereochemistry was not assigned.

Workup

  1. customExample 40 was synthesized
  2. customas described for the synthesis of Example 1

Sources & evidence

ORD record
ord-1aad2294bdd04d08a3b8f6d51465b330
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

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