Methanesulfonic Acid → HCID 118451728, compound

HRID 632592Notes

Reaction equation

HRID 632592 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(OC(C)C)(=O)C.[CH3:60][S:61](O)(=[O:63])=[O:62]>O>[CH3:60][S:61]([O:18][C@H:16]1[CH2:15][C:14]([CH3:19])([CH3:20])[CH2:13][C:12]2[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]([C@@H:40]([F:51])[C:41]3[CH:46]=[CH:45][C:44]([C:47]([F:49])([F:48])[F:50])=[CH:43][CH:42]=3)=[C:8]([CH:5]3[CH2:4][CH2:3][C:2]([F:1])([F:52])[CH2:7][CH2:6]3)[C:17]1=2)(=[O:63])=[O:62]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 7915Isopropyl AcetateHCID 71656881HCID 71656881, compound

Product 1

HCID 118451728HCID 118451728, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 40.7 mg (0.055 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, 0.28 ml of isopropyl acetate and 0.008 ml of ultrapure water were added, and the reaction mixture was stirred at room temperature to obtain a homogeneous solution. Then, 0.004 ml (0.062 mmol) of methanesulfonic acid was added thereto, and the reaction mixture was stirred at the same temperature for 90 minutes. The precipitated solid was obtained by filtration, washed with 0.04 ml of isopropyl acetate three times and then dried under reduced pressure at 40° C. to provide 38.7 mg of the title compound as a white powder (yield: 85%).

Workup

  1. additionwere added
  2. customto obtain a homogeneous solution
  3. stirringthe reaction mixture was stirred at the same temperature for 90 minutes
  4. customThe precipitated solid was obtained by filtration
  5. washwashed with 0.04 ml of isopropyl acetate three times
  6. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-b2373a950d1f4216928b2577c5aa687d
Source dataset
uspto-grants-2016_04
Patent number
US09321747B2

Reaction notes

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