Hydrochloric Acid → N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]amino}propyl]-1-oxo-2-(1-propylbutyl)-1,2-dihydroisoquinoline-5-carboxamide hydrochloride

HRID 1661085Notes

Reaction equation

HRID 1661085 reaction equation
[CH2:1]([C@H:8]([NH:24][C:25]([C:27]1[C:28]2[CH:29]=[CH: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:9]([OH:23])[CH2:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:45]>C(OCC)C.O1CCOCC1>[ClH:45].[CH2:1]([C@H:8]([NH:24][C:25]([C:27]1[C:28]2[CH:29]=[CH: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:9]([OH:23])[CH2:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:22])[F:20])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 25204518N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]-amino}propyl]-1-oxo-2-(1-propylbutyl)-1,2-dihydroisoquinoline-5-carboxamide

Product 1

HCID 67429965N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]amino}propyl]-1-oxo-2-(1-propylbutyl)-1,2-dihydroisoquinoline-5-carboxamide hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

84 mg of N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]-amino}propyl]-1-oxo-2-(1-propylbutyl)-1,2-dihydroisoquinoline-5-carboxamide are dissolved in 4 cm3 of ethyl ether at a temperature close to 20° C. 0.2 cm3 of a 4M solution of hydrochloric acid in dioxane is added while stirring and under argon. The reaction mixture precipitates. The stirring is stopped. The supernatant is removed and 5 cm3 of ethyl ether are added. This operation is carried out three times. The last suspension is concentrated under reduced pressure (5 kPa). 87 mg of N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]amino}propyl]-1-oxo-2-(1-propylbutyl)-1,2-dihydroisoquinoline-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. customThe supernatant is removed
  4. addition5 cm3 of ethyl ether are added
  5. concentrationThe last suspension is concentrated under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-e57830f8a2ee4b49b8ce8b3dfe0ab92a
Source dataset
uspto-grants-2011_10
Patent number
US08030320B2

Reaction notes

Loading…