Hydrochloric Acid → HCID 25206781, compound

HRID 387682Notes

Reaction equation

HRID 387682 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]([CH3:37])[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.[ClH:50]>C(OCC)C.O1CCOCC1>[ClH:50].[F:49][C:47]1[CH:46]=[C:4]([CH:3]=[C:2]([F:1])[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]([CH3:37])[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 25206782HCID 25206782, compound

Product 1

HCID 25206781HCID 25206781, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

68 mg of N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-7-methyl-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide are dissolved, under an argon atmosphere, in 5 cm3 of ethyl ether. 0.2 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 10 cm3 of ethyl ether, concentrated to dryness under reduced pressure (5 kPa), and dried under vacuum at a temperature of 35° C. 69 mg of N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-7-methyl-1-oxo-2-(1-propyl butyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide hydrochloride (1:1) are obtained in the form of a white 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-528437c4f526492fba3ee9106b155741
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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