Benzenesulfonic Acid → HCID 131735435, compound

HRID 632590Notes

Reaction equation

HRID 632590 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]1([S:59](O)(=[O:61])=[O:60])[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>COC(C)(C)C>[C:53]1([S:59]([O:18][C@H:16]2[CH2:15][C:14]([CH3:19])([CH3:20])[CH2:13][C:12]3[N:11]=[C:10]([CH:21]4[CH2:22][CH2:23][N:24]([C:27]5[N:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][C:36]([OH:39])([CH3:37])[CH3:38])=[CH:29][N:28]=5)[CH2:25][CH2:26]4)[C:9]([C@@H:40]([F:51])[C:41]4[CH:46]=[CH:45][C:44]([C:47]([F:49])([F:48])[F:50])=[CH:43][CH:42]=4)=[C:8]([CH:5]4[CH2:4][CH2:3][C:2]([F:1])([F:52])[CH2:7][CH2:6]4)[C:17]2=3)(=[O:61])=[O:60])[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

4

Reactant 2

HCID 7371Benzenesulfonic AcidHCID 71656881HCID 71656881, compound

Product 1

HCID 131735435HCID 131735435, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 30.0 mg (0.0408 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 0.4 ml of tert-butyl methyl ether, 0.013 ml (0.041 mmol) of 3.16 M benzenesulfonic acid aqueous solution was added dropwise with stirring at 40° C. Then, the reaction mixture was cooled to room temperature and stirred for 30 minutes. The precipitated solid was obtained by filtration, washed with tert-butyl methyl ether and then dried under reduced pressure at 60° C. to provide 29.8 mg of the title compound as a white powder (yield: 82%).

Workup

  1. temperatureThen, the reaction mixture was cooled to room temperature
  2. stirringstirred for 30 minutes
  3. customThe precipitated solid was obtained by filtration
  4. washwashed with tert-butyl methyl ether
  5. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-4b9a5dde98a64cbfa476acc90c3c11c2
Source dataset
uspto-grants-2016_04
Patent number
US09321747B2

Reaction notes

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