Acetone → HCID 71657068, compound

HRID 632591Notes

Reaction equation

HRID 632591 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.[C:53]([OH:60])(=[O:59])/[CH:54]=[CH:55]/[C:56]([OH:58])=[O:57].CC(C)=O>O>[C:53]([OH:60])(=[O:59])/[CH:54]=[CH:55]/[C:56]([OH:58])=[O:57].[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.[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]([CH3:37])([OH:39])[CH3:38])=[CH:29][N:28]=4)[CH2:25][CH2:26]3)[C:9]=2[C@H:40]([C:41]2[CH:42]=[CH:43][C:44]([C:47]([F:48])([F:49])[F:50])=[CH:45][CH:46]=2)[F:51])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 444972Fumaric AcidHCID 71656881HCID 71656881, compound

Product 1

HCID 71657068HCID 71657068, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 40.0 mg (0.054 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, and 3.3 mg (0.028 mmol) of fumaric acid, 0.08 ml of acetone and 0.008 ml of ultrapure water were added, and the reaction mixture was stirred at room temperature to obtain a homogeneous solution. Subsequently, a small amount of a seed crystal was added thereto, and then the reaction mixture was stirred for 30 minutes under ice cooling. The precipitated solid was obtained by filtration, washed with 0.04 ml of acetone and then dried under reduced pressure at 40° C. to provide 35.6 mg of the title compound as a white powder (yield: 77%).

Workup

  1. additionwere added
  2. customto obtain a homogeneous solution
  3. additionSubsequently, a small amount of a seed crystal was added
  4. stirringthe reaction mixture was stirred for 30 minutes under ice cooling
  5. customThe precipitated solid was obtained by filtration
  6. washwashed with 0.04 ml of acetone
  7. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-ff73f4cadb34454c979c82550c62fa57
Source dataset
uspto-grants-2016_04
Patent number
US09321747B2

Reaction notes

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