(S)-3-(1-amino-isoquinolin-6-yloxy)piperidin-1-carboxylic acid tert-butyl ester → Ammonia

HRID 1435965Notes

Reaction equation

HRID 1435965 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21]([NH2:25])=[N:20][CH:19]=[CH:18]3)[CH2:9]1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[NH3:8].[NH:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21]([NH2:25])=[N:20][CH:19]=[CH:18]3)[CH2:9]1

Participants

5

Reactant 1

HCID 68875514(S)-3-(1-amino-isoquinolin-6-yloxy)piperidin-1-carboxylic acid tert-butyl ester

Product 2

HCID 222AmmoniaYield 1%HCID 16222570(S)-6-(piperidin-3-yloxy)-isoquinolin-1-ylamine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of (S)-3-(1-amino-isoquinolin-6-yloxy)piperidin-1-carboxylic acid tert-butyl ester (72 mg) in dichloromethane (2 ml) and trifluoroacetic acid (1 ml) was stirred at ambient temperature for 1.5 h. The mixture was concentrated in vacuo then flash chromatography of the residue (eluent: 2-10% methanol in dichloromethane with 1% aqueous ammonia) gave (S)-6-(piperidin-3-yloxy)-isoquinolin-1-ylamine, El-MS: m/z=244.4 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-71ae303c31cf498dab37b7fd0d8e2d1a
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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