Hydrochloric Acid → 6-(3-Amino-cyclobutoxy)-7-chloro-2H-isoquinolin-1-one

HRID 402541Notes

Reaction equation

HRID 402541 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:20][CH:21]3[CH2:24][CH:23]([NH2:25])[CH2:22]3)=[C:16]([Cl:19])[CH:17]=2)[CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1.Cl>CC(O)C>[NH2:25][CH:23]1[CH2:24][CH:21]([O:20][C:15]2[CH:14]=[C:13]3[C:18](=[CH:17][C:16]=2[Cl:19])[C:9](=[O:8])[NH:10][CH:11]=[CH:12]3)[CH2:22]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 592248403-(1-Benzyloxy-7-chloro-isoquinolin-6-yloxy)-cyclobutylamine

Product 1

HCID 592248436-(3-Amino-cyclobutoxy)-7-chloro-2H-isoquinolin-1-oneYield 69.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 377 mg (1.06 mmol) of 3-(1-benzyloxy-7-chloro-isoquinolin-6-yloxy)-cyclobutylamine (51) in 8 mL of 2-propanol was treated with 8 mL of 2N aqueous hydrochloric acid and stirred until complete conversion. The reaction mixture was evaporated, twice lyophilized from water and recrystallized from 2-propanol. 195 mg of the title compound could be isolated as hydrochloride as unseparable mixture of diastereoisomers. Rt=1.92 min (Method G). Detected mass: 265.1 (M+H+).

Workup

  1. customThe reaction mixture was evaporated
  2. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-f440d8c94dec49089c6f0e613bd6fae6
Source dataset
uspto-grants-2014_06
Patent number
US08742116B2

Reaction notes

Loading…