Hydrochloric Acid → HCID 86644021, compound

HRID 387660Notes

Reaction equation

HRID 387660 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:47]=[C:48]([F:50])[CH:49]=1)[CH2:5][C@H:6]([NH:24][C:25]([C:27]1[C:28]2[CH2:29][CH2:30][N:31]([CH:38]([C:40]3[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=3)[CH3:39])[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:51]>CO.C(OCC)C>[ClH:51].[F:1][C:2]1[CH:3]=[C:4]([CH:47]=[C:48]([F:50])[CH:49]=1)[CH2:5][C@H:6]([NH:24][C:25]([C:27]1[C:28]2[CH2:29][CH2:30][N:31]([CH:38]([C:40]3[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=3)[CH3:39])[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)[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86644022HCID 86644022, compound

Product 1

HCID 86644021HCID 86644021, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

202 mg of N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-2-[1-(4-fluorophenyl)ethyl]-1-oxo-1,2,3,4-tetrahydroisoquinoline-5-carboxamide are dissolved in a mixture containing ethyl ether and a few drops of methanol at a temperature close to 20° C. 5 cm3 of a 1M solution of hydrochloric acid in ethyl ether are added. The reaction mixture is concentrated using a rotary evaporator under reduced pressure (5 kPa). The solid obtained is triturated in diisopropyl ether, filtered and dried. 206 mg of N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-2-[1-(4-fluorophenyl)ethyl]-1-oxo-1,2,3,4-tetrahydroisoquinoline-5-carboxamide hydrochloride (1:1) are obtained in the form of an amorphous white solid.

Workup

  1. customclose to 20° C
  2. concentrationThe reaction mixture is concentrated
  3. customa rotary evaporator under reduced pressure (5 kPa)
  4. customThe solid obtained
  5. customis triturated in diisopropyl ether
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-1c32f14863e74764b1f1f57dbac9767d
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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