2-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane → Methyl 3-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoro methyl)pentyl]amino}-1h-indazol-1-yl)benzoate

HRID 418800Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][O:11]2)[CH:7]=1.[NH2:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:23]=1[CH:24]=[N:25][N:26]2[C:31]1[CH:32]=[C:33]([CH:38]=[CH:39][CH:40]=1)[C:34]([O:36][CH3:37])=[O:35]>CS(C)=O.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]([OH:11])([C:13]([F:16])([F:15])[F:14])[CH2:12][NH:21][C:22]2[CH:30]=[CH:29][CH:28]=[C:27]3[C:23]=2[CH:24]=[N:25][N:26]3[C:31]2[CH:32]=[C:33]([CH:38]=[CH:39][CH:40]=2)[C:34]([O:36][CH3:37])=[O:35])[CH:7]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of racemic 2-{2-[5-fluoro-2-(methyloxy)phenyl]-2-methylpropyl}-2-(trifluoromethyl)oxirane (which may be prepared according to WO 04/063163, 35 mg, 0.12 mmol) and methyl 3-(4-amino-1H-indazol-1-yl)benzoate (Intermediate 9) (32.7 mg, 0.12 mmol) was heated by microwave (250 W) at 170° C. for 45 minutes. The crude product was cooled, dissolved in DMSO/MeOH and purified by mass-directed autopreparation. The appropriate fractions were evaporated, dissolved in DCM, washed with aqueous sodium bicarbonate, passed through a hydrophobic frit and evaporated to give the title compound (16.7 mg).

Workup

custompurified by mass-directed autopreparation
customThe appropriate fractions were evaporated
dissolutiondissolved in DCM
washwashed with aqueous sodium bicarbonate
customevaporated

Sources & evidence

ORD record: ord-5f2d6fbba6a745729054efa8dda8b744
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093281B2

Reaction notes

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