Hydrogen Bromide → HCID 71656882, compound

HRID 632587Notes

Reaction equation

HRID 632587 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.[BrH:53]>CC(C)=O>[BrH: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 260Hydrogen BromideHCID 71656881HCID 71656881, compound

Product 1

HCID 71656882HCID 71656882, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 50.0 mg (0.068 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 0.1 ml of acetone, 0.008 ml (0.069 mmol) of 47% hydrobromic acid was added at room temperature. Subsequently, a small amount of a seed crystal was added thereto, and the reaction mixture was stirred for 50 minutes. The precipitated solid was obtained by filtration, washed with 0.1 ml of acetone five times and then dried under reduced pressure at 40° C. to provide 38.1 mg of the title compound as a white powder (yield: 69%).

Workup

  1. additionSubsequently, a small amount of a seed crystal was added
  2. customThe precipitated solid was obtained by filtration
  3. washwashed with 0.1 ml of acetone five times
  4. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-f4915aaa85b043a195c7dbfebf2da7ea
Source dataset
uspto-grants-2016_04
Patent number
US09321747B2

Reaction notes

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