Hydrogen Bromide → HCID 117687878, compound

HRID 632601Notes

Reaction equation

HRID 632601 reaction equation
[BrH:1].[C:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:12]=[N:13][C:14]([N:17]3[CH2:22][CH2:21][CH:20]([C:23]4[C:32]([C@@H:33]([F:44])[C:34]5[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=5)=[C:31]([CH:45]5[CH2:50][CH2:49][C:48]([F:52])([F:51])[CH2:47][CH2:46]5)[C:30]5[C@@H:29]([OH:53])[CH2:28][C:27]([CH3:55])([CH3:54])[CH2:26][C:25]=5[N:24]=4)[CH2:19][CH2:18]3)=[N:15][CH:16]=2)[CH:8]=[CH:9][CH:10]=1)([OH:4])=[O:3]>CC(C)=O>[BrH:1].[BrH:1].[C:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[N:15][C:14]([N:17]3[CH2:22][CH2:21][CH:20]([C:23]4[C:32]([C@@H:33]([F:44])[C:34]5[CH:39]=[CH:38][C:37]([C:40]([F:41])([F:42])[F:43])=[CH:36][CH:35]=5)=[C:31]([CH:45]5[CH2:50][CH2:49][C:48]([F:51])([F:52])[CH2:47][CH2:46]5)[C:30]5[C@@H:29]([OH:53])[CH2:28][C:27]([CH3:55])([CH3:54])[CH2:26][C:25]=5[N:24]=4)[CH2:19][CH2:18]3)=[N:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)([OH:4])=[O:3]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 71657276HCID 71657276, compound

Product 1

HCID 117687878HCID 117687878, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Reactions similar to those of Example 13 were performed except for using 15.2 μl (134 μmol) of 47% hydrobromic acid instead of 35% hydrochloric acid and using 0.45 ml of acetone, and from 45.7 mg (60.7 μmol) of (5S)-2-{1-[5-(3-Carboxyphenyl)pyrimidin-2-yl]piperidin-4-yl}-4-(4,4-difluorocyclohexyl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol, which was prepared by a method similar to that of Reference Example 30, 27.2 mg of the title compound was obtained as a white powder (yield: 49%).

Sources & evidence

ORD record
ord-8af24d20df1a4db6b1888f7f1dd44298
Source dataset
uspto-grants-2016_04
Patent number
US09321747B2

Reaction notes

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