Hydrochloric Acid → N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide hydrochloride

HRID 387627Notes

Reaction equation

HRID 387627 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:45]=[C:46]([F:48])[CH:47]=1)[CH2:5][C@H:6]([NH:24][C:25]([C:27]1[C:28]2[CH2:29][CH2:30][N:31]([CH:38]([CH2:42][CH2:43][CH3:44])[CH2:39][CH2:40][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:49]>C(OCC)C>[ClH:49].[F:1][C:2]1[CH:3]=[C:4]([CH:45]=[C:46]([F:48])[CH:47]=1)[CH2:5][C@H:6]([NH:24][C:25]([C:27]1[C:28]2[CH2:29][CH2:30][N:31]([CH:38]([CH2:39][CH2:40][CH3:41])[CH2:42][CH2:43][CH3:44])[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:21])([F:20])[F:22])[CH:14]=2)[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 25206289HCID 25206289, compound

Product 1

HCID 25206288N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

40 mg of N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide are dissolved in 10 cm3 of ethyl ether at a temperature close to 20° C. 3 cm3 of a 1M hydrochloric acid solution in ether are added while stirring under argon. The reaction mixture precipitates. The precipitate is filtered through sintered glass, washed with 3 lots of 5 cm3 of ethyl ether then dried in a desiccator under vacuum at 35° C. for 2 h. 129 mg of N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide hydrochloride (1:1) are obtained in the form of a white solid.

Workup

  1. customclose to 20° C
  2. customThe reaction mixture precipitates
  3. filtrationThe precipitate is filtered through sintered glass
  4. washwashed with 3 lots of 5 cm3 of ethyl ether
  5. customthen dried in a desiccator under vacuum at 35° C. for 2 h

Sources & evidence

ORD record
ord-bff53b1f390540749d0896dc2a466744
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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