4-(1-Benzyloxy-7-chloro-isoquinolin-6-yloxy)-piperidine-1-carboxylic acid tert-butyl-ester → 7-Chloro-6-(piperidin-4-yloxy)isoquinolin-1(2H)-one

HRID 1930214Notes

Reaction equation

HRID 1930214 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][C:24]=2[Cl:25])[C:21]([O:26]CC2C=CC=CC=2)=[N:20][CH:19]=[CH:18]3)[CH2:10][CH2:9]1)=O)(C)(C)C>CO>[Cl:25][C:24]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][NH:20][C:21]2=[O:26])=[CH:16][C:15]=1[O:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

3

Reactant 1

HCID 576525114-(1-Benzyloxy-7-chloro-isoquinolin-6-yloxy)-piperidine-1-carboxylic acid tert-butyl-ester

Product 1

HCID 576524487-Chloro-6-(piperidin-4-yloxy)isoquinolin-1(2H)-oneYield 39.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

254 mg (0.52 mmol) of 4-(1-benzyloxy-7-chloro-isoquinolin-6-yloxy)-piperidine-1-carboxylic acid tert-butyl-ester (53) were stirred in methanol/2 N HCl (1:1) at room temperature overnight. The solvent was removed i. vac. and the residue was purified by preparative HPLC. The product fractions were evaporated and dissolved in 2 N HCl. Lyophilization results in 57 mg of the desired compound as hydrochloride. Rt=0.95 min (Method B). Detected mass: 279.1 (M+H+).

Workup

  1. customThe solvent was removed i
  2. customand the residue was purified by preparative HPLC
  3. customThe product fractions were evaporated
  4. dissolutiondissolved in 2 N HCl

Sources & evidence

ORD record
ord-73a5e656c067423683c397e8c9906a48
Source dataset
uspto-grants-2012_05
Patent number
US08188117B2

Reaction notes

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