Trifluoroacetic acid → HCID 86682452, compound

HRID 715876Notes

Reaction equation

HRID 715876 reaction equation
[F:1][C:2]1([F:62])[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[CH:16]([O:18]CC4C=CC(OC)=CC=4)[CH2:15][C:14]([CH3:29])([CH3:28])[CH2:13][C:12]=3[N:11]=[C:10]([CH:30]3[CH2:35][CH2:34][N:33]([C:36]4[N:41]=[CH:40][C:39]([O:42][CH:43]5[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]5)=[CH:38][N:37]=4)[CH2:32][CH2:31]3)[C:9]=2[CH:50]([F:61])[C:51]2[CH:56]=[CH:55][C:54]([C:57]([F:60])([F:59])[F:58])=[CH:53][CH:52]=2)[CH2:4][CH2:3]1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[F:62][C:2]1([F:1])[CH2:3][CH2:4][CH:5]([C:8]2[C:17]3[CH:16]([OH:18])[CH2:15][C:14]([CH3:29])([CH3:28])[CH2:13][C:12]=3[N:11]=[C:10]([CH:30]3[CH2:35][CH2:34][N:33]([C:36]4[N:37]=[CH:38][C:39]([O:42][CH:43]5[CH2:44][CH2:45][N:46]([CH3:49])[CH2:47][CH2:48]5)=[CH:40][N:41]=4)[CH2:32][CH2:31]3)[C:9]=2[CH:50]([F:61])[C:51]2[CH:52]=[CH:53][C:54]([C:57]([F:58])([F:60])[F:59])=[CH:55][CH:56]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86682453HCID 86682453, compound

Product 1

HCID 86682452HCID 86682452, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 86 mg (99 μmol) of 4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-2-(1-{5-[(1-methylpiperidin-4-yl)oxy]pyrimidin-2-yl}piperidin-4-yl)-5,6,7,8-tetrahydroquinoline, which was prepared by a method similar to that of Reference Example 29, in 1.0 ml of dichloromethane, 0.2 ml of anisole and 0.2 ml of trifluoroacetic acid were added, and the reaction solution was stirred at room temperature for 12 hours. After completion of the reaction, the solvent in the reaction solution and trifluoroacetic acid were distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [dichloromethane/methanol/28% ammonia water=100/0/0-90/9.5/0.5 (V/V/V)] and thin layer chromatography [dichloromethane/methanol/28% ammonia water=90/9.5/0.5 (V/V/V)] to provide 12 mg of the title compound as a white solid (yield: 17%).

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent in the reaction solution and trifluoroacetic acid were distilled off under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography [dichloromethane/methanol/28% ammonia water=100/0/0-90/9.5/0.5 (V/V/V)] and thin layer chromatography [dichloromethane/methanol/28% ammonia water=90/9.5/0.5 (V/V/V)]

Sources & evidence

ORD record
ord-3777938e4f8943b69acf871191384018
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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