Water → HCID 71656972, compound

HRID 632589Notes

Reaction equation

HRID 632589 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])[CH2:54][CH2:55][C:56]([OH:58])=[O:57].O>CC(C)=O>[C:53]([OH:60])(=[O:59])[CH2:54][CH2:55][C:56]([OH:58])=[O:57].[C:53]([OH:60])(=[O:59])[CH2:54][CH2:55][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

Participants

5

Reactant 3

HCID 962WaterHCID 1110Succinic AcidHCID 71656881HCID 71656881, compound

Product 1

HCID 71656972HCID 71656972, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To 40.8 mg (0.056 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 13.1 mg (0.11 mmol) of succinic 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. A small amount of a seed crystal was added thereto, then 0.02 ml of acetone was added, and the reaction mixture was stirred for 30 minutes. The precipitated solid was obtained by filtration, washed with 0.4 ml of acetone and then dried under reduced pressure at 40° C. to provide 18.7 mg of the title compound as a white powder (yield: 39%).

Workup

  1. additionwere added
  2. customto obtain a homogeneous solution
  3. additionA small amount of a seed crystal was added
  4. stirringthe reaction mixture was stirred for 30 minutes
  5. customThe precipitated solid was obtained by filtration
  6. washwashed with 0.4 ml of acetone
  7. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-faacc259d8ee4ea6a2cb5a33200e5fe4
Source dataset
uspto-grants-2016_04
Patent number
US09321747B2

Reaction notes

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