Ammonia → HCID 86642508, compound

HRID 2074927Notes

Reaction equation

[F:1][C:2]([F:53])([F:52])[C:3]1[CH:4]=[C:5]([C:13]([CH3:51])([CH3:50])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:32]3[CH2:37][CH2:36][N:35]4[CH2:38][CH2:39][CH2:40][C@H:34]4[C@@H:33]3[CH2:41][O:42][Si](C(C)(C)C)(C)C)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.N>CO.Cl>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]([CH3:51])([CH3:50])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:32]3[CH2:37][CH2:36][N:35]4[CH2:38][CH2:39][CH2:40][C@H:34]4[C@@H:33]3[CH2:41][OH:42])=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:4]=[C:3]([C:2]([F:1])([F:52])[F:53])[CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of cis-2-[3,5-bis(trifluoromethyl)phenyl]-N-[6-[1-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-4-(4-fluoro-2-methylphenyl)-3-pyridinyl]-N,2-dimethylpropanamide (D74, 10.5 mg) in dry methanol (1 mL) at 0° C., one drop of concentrated HCl was added. The resulting mixture was stirred at 0° C. for 1.5 hours and then was allowed to reach rt and stirred at this temperature for 2 hours. The solution was then directly charged onto a SCX cartridge (eluting with MeOH and ammonia, 0.5N solution in methanol) to give the desired compound (4.5 mg) as yellow oil.

Workup

customto reach rt
stirringstirred at this temperature for 2 hours

Sources & evidence

ORD record: ord-10dda1cbacec4d69ae73a1fead72dbca
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919491B2

Reaction notes

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