Hydrochloric Acid → HCID 25206783, compound

HRID 387685Notes

Reaction equation

HRID 387685 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:46]=[C:47]([F:49])[CH:48]=1)[CH2:5][C@H:6]([NH:24][C:25]([C:27]1[C:28]2[CH2:29][CH2:30][N:31]([CH:39]([CH2:43][CH2:44][CH3:45])[CH2:40][CH2:41][CH3:42])[C:32](=[O:38])[C:33]=2[CH:34]=[C:35]([Cl:37])[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.Cl>C(OCC)C.O1CCOCC1>[ClH:37].[F:1][C:2]1[CH:3]=[C:4]([CH:46]=[C:47]([F:49])[CH:48]=1)[CH2:5][C@H:6]([NH:24][C:25]([C:27]1[C:28]2[CH2:29][CH2:30][N:31]([CH:39]([CH2:40][CH2:41][CH3:42])[CH2:43][CH2:44][CH3:45])[C:32](=[O:38])[C:33]=2[CH:34]=[C:35]([Cl:37])[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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 25206784HCID 25206784, compound

Product 1

HCID 25206783HCID 25206783, compoundYield 193.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

272 mg of N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-7-chloro-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide are dissolved, under an argon atmosphere, in 5 cm3 of ethyl ether. 0.35 cm3 of a 4N solution of hydrochloric acid in dioxane is added, while stirring, at a temperature of 20° C. The reaction mixture is concentrated to dryness under reduced pressure (5 kPa). The residue is taken up with two lots of 10 cm3 of diisopropyl ether, concentrated to dryness under reduced pressure (5 kPa), and dried under vacuum at a temperature of 35° C. 277 mg of N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-7-chloro-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide hydrochloride (1:1) are obtained in the form of a beige powder.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (5 kPa)
  2. concentrationconcentrated to dryness under reduced pressure (5 kPa)
  3. customdried under vacuum at a temperature of 35° C

Sources & evidence

ORD record
ord-9c060d1410464c5ba1760b7ca40bf55f
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

Loading…