Ether hydrochloride → 1-{[4-(Isoquinolin-1-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester, bis hydrochloride

HRID 346925Notes

Reaction equation

HRID 346925 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([O:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][N:15]=2)[CH2:10][CH:9]1[C:24](=[O:36])[NH:25][C:26]1([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:28][CH:27]1[CH:29]=[CH2:30])=O)(C)(C)C.[ClH:37].CCOCC>>[ClH:37].[ClH:37].[CH2:34]([O:33][C:31]([C:26]1([NH:25][C:24]([CH:9]2[CH2:10][CH:11]([O:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=[CH:16][N:15]=3)[CH2:12][NH:8]2)=[O:36])[CH2:28][CH:27]1[CH:29]=[CH2:30])=[O:32])[CH3:35]

Participants

3

Reactant 2

HCID 10953452Ether hydrochlorideHCID 68747060HCID 68747060, compound

Product 1

HCID 1317262291-{[4-(Isoquinolin-1-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester, bis hydrochlorideYield 100%

Procedure

A stirred slurry of 2-(1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(isoquinolin-1-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (5.40 g, 10.9 mmol) was treated with 2N HCl/ether (Aldrich)(250 mL) for 24 h. The reaction mixture was concentrated in vacuo to give 5.3 g (˜100%) of 1-{[4-(isoquinolin-1-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester, bis hydrochloride as a white solid: LC-MS (Method A, retention time: 2.40 min), MS m/z 396 (M++1).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-e3b5a5ed117940c2b4a80209202c1c4e
Source dataset
uspto-grants-2007_02
Patent number
US07173004B2

Reaction notes

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