Hydrochloric Acid → HCID 25206444, compound

HRID 387646Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[C:43]([F:45])[CH:44]=1)[CH2:5][C@H:6]([NH:24][C:25]([C:27]1[C:28]2[CH2:29][CH2:30][N:31]([CH2:38][CH2:39][O:40][CH3:41])[C:32](=[O:37])[C:33]=2[CH:34]=[CH:35][CH:36]=1)=[O:26])[C@H:7]([OH:23])[CH2:8][NH:9][C:10]1([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[CH2:12][CH2:11]1.[ClH:46]>O1CCOCC1.C(OCC)C>[ClH:46].[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[C:43]([F:45])[CH:44]=1)[CH2:5][C@H:6]([NH:24][C:25]([C:27]1[C:28]2[CH2:29][CH2:30][N:31]([CH2:38][CH2:39][O:40][CH3:41])[C:32](=[O:37])[C:33]=2[CH:34]=[CH:35][CH:36]=1)=[O:26])[C@H:7]([OH:23])[CH2:8][NH:9][C:10]1([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[CH2:11][CH2:12]1

Participants

Conditions

Temperature: 20 °C

Procedure

79 mg of N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-2-(2-methoxyethyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-5-carboxamide are dissolved in 2 cm3 of dioxane at a temperature close to 20° C. 1 cm3 of a 4M solution of hydrochloric acid in ethyl ether is added while stirring under argon, at a temperature of 20° C. The reaction mixture is concentrated under vacuum at a temperature of 40° C. 83 mg of N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-2-(2-methoxyethyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-5-carboxamide hydrochloride (1:1) are obtained in the form of a white powder.

Workup

customclose to 20° C
concentrationThe reaction mixture is concentrated under vacuum at a temperature of 40° C

Sources & evidence

ORD record: ord-98e80bc9aade4514977c6bcf5019086e
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372864B2

Reaction notes

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