Hydrochloric Acid → (5S)-4-(4,4-Difluorocyclohexyl)-2-[1-(5-{[(2S)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol dihydrochloride

HRID 632593Notes

Reaction equation

HRID 632593 reaction equation
[F:1][C:2]1([F:51])[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][C@@H:35]([OH:38])[CH2:36][OH:37])=[CH:29][N:28]=4)[CH2:23][CH2:22]3)[C:9]=2[C@@H:39]([F:50])[C:40]2[CH:45]=[CH:44][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:42][CH:41]=2)[CH2:4][CH2:3]1.[ClH:52]>CC(C)=O>[ClH:52].[ClH:52].[F:51][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[CH2:26][CH2:25][N:24]([C:27]4[N:32]=[CH:31][C:30]([O:33][CH2:34][C@@H:35]([OH:38])[CH2:36][OH:37])=[CH:29][N:28]=4)[CH2:23][CH2:22]3)[C:9]=2[C@@H:39]([F:50])[C:40]2[CH:45]=[CH:44][C:43]([C:46]([F:47])([F:49])[F:48])=[CH:42][CH:41]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71657166HCID 71657166, compound

Product 1

HCID 71657165(5S)-4-(4,4-Difluorocyclohexyl)-2-[1-(5-{[(2S)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol dihydrochlorideYield 66%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 36.2 mg (50.1 μmol) of (5S)-4-(4,4-Difluorocyclohexyl)-2-[1-(5-{[(2S)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol, which was prepared by a method similar to that of Reference Example 25, in 0.36 ml of acetone, 9.2 μl (110 μmol) of 35% hydrochloric acid was added dropwise with stirring at 45° C., and the mixture was stirred for 10 minutes. Then, stirring was continued at room temperature for 30 minutes, and the precipitated solid was obtained by filtration, washed with acetone and then dried under reduced pressure at 40° C. to provide 26.3 mg of the title compound as a white powder (yield: 66%).

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. stirringThen, stirring
  3. customthe precipitated solid was obtained by filtration
  4. washwashed with acetone
  5. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-f06fea0f3c4f40419df3476b96f6500d
Source dataset
uspto-grants-2016_04
Patent number
US09321747B2

Reaction notes

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