Hydrochloric Acid → HCID 71656880, compound

HRID 632586Notes

Reaction equation

HRID 632586 reaction equation
[F:1][C:2]1([F:52])[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[C@@H:16]([OH:18])[CH2:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]=3[N:11]=[C:10]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]4[N:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][C:36]([OH:39])([CH3:38])[CH3:37])=[CH:29][N:28]=4)[CH2:23][CH2:22]3)[C:9]=2[C@@H:40]([F:51])[C:41]2[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][CH:42]=2)[CH2:4][CH2:3]1.[ClH:53]>CC(C)=O>[ClH:53].[F:52][C:2]1([F:1])[CH2:3][CH2:4][CH:5]([C:8]2[C:17]3[C@@H:16]([OH:18])[CH2:15][C:14]([CH3:19])([CH3:20])[CH2:13][C:12]=3[N:11]=[C:10]([CH:21]3[CH2:22][CH2:23][N:24]([C:27]4[N:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][C:36]([OH:39])([CH3:37])[CH3:38])=[CH:29][N:28]=4)[CH2:25][CH2:26]3)[C:9]=2[C@@H:40]([F:51])[C:41]2[CH:46]=[CH:45][C:44]([C:47]([F:48])([F:50])[F:49])=[CH:43][CH:42]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71656881HCID 71656881, compound

Product 1

HCID 71656880HCID 71656880, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 270 mg (0.367 mmol) of (5S)-4-(4,4-Difluorocyclohexyl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-2-{1-[5-(3-hydroxy-3-methylbutoxy)pyrimidin-2-yl]piperidin-4-yl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol, which was prepared by a method similar to that of Reference Example 16, in 0.54 ml of acetone, 0.0322 ml (0.386 mmol) of 35% hydrochloric acid was added at room temperature, and the mixture was stirred. This solution was left standing overnight at −20° C. After precipitation of a solid, the reaction solution was further stirred at room temperature for 1 hour. The solid was obtained by filtration, washed with a 1:1 mixed solvent of acetone and tert-butyl methyl ether and then dried under reduced pressure at 40° C. to provide 179 mg of the title compound as a white powder (yield: 63%).

Workup

  1. waitThis solution was left
  2. customAfter precipitation of a solid
  3. stirringthe reaction solution was further stirred at room temperature for 1 hour
  4. customThe solid was obtained by filtration
  5. washwashed with a 1:1 mixed solvent of acetone and tert-butyl methyl ether
  6. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-087e626328834cb98521806158d8769f
Source dataset
uspto-grants-2016_04
Patent number
US09321747B2

Reaction notes

Loading…