4-(5-Tributylstannanyl-[1,2,3]triazol-1-yl)-benzonitrile → 6-[1-(4-Cyano-phenyl)-1H-1,2,3-triazol-5-yl]-N,5-dimethyl-3-oxo-4-[3-(trifluoromethyl)-phenyl]-3,4-dihydro-pyrazine-2-carboxamide

HRID 1958296Notes

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]1[N:10]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[N:9]=[N:8][CH:7]=1)CCC.Br[C:28]1[N:33]=[C:32]([C:34]([NH:36][CH3:37])=[O:35])[C:31](=[O:38])[N:30]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([F:48])([F:47])[F:46])[CH:40]=2)[C:29]=1[CH3:49]>COCCOC>[C:15]([C:14]1[CH:13]=[CH:12][C:11]([N:10]2[C:6]([C:28]3[N:33]=[C:32]([C:34]([NH:36][CH3:37])=[O:35])[C:31](=[O:38])[N:30]([C:39]4[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([F:46])([F:47])[F:48])[CH:40]=4)[C:29]=3[CH3:49])=[CH:7][N:8]=[N:9]2)=[CH:18][CH:17]=1)#[N:16]

Participants

Conditions

Temperature: 100 °C

Procedure

4-(5-Tributylstannanyl-[1,2,3]triazol-1-yl)-benzonitrile (0.15 g, 0.32 mmol), 6-bromo-N,5-dimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide (SM2, 0.054 g, 0.14 mmol), Pd(PBut3)2 (10 mg) and DME (2 ml) were placed in a tube for microwave synthesis. The mixture was degassed with argon and heated in a synthesis microwave heater (CEM) at 100° C. (max 150 W) for 10 minutes. The solvent was removed in vacuo giving a crude product which was purified on silica and then further purified on preparative HPLC. The pure fractions were freeze-dried giving 27 mg (41%) of the title compound.

Workup

customThe mixture was degassed with argon
customThe solvent was removed in vacuo
customgiving a crude product which
customwas purified on silica
customfurther purified on preparative HPLC
customThe pure fractions were freeze-dried

Sources & evidence

ORD record: ord-13f325bcf08542e391a6a400e2cc4e9b
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410114B2

Reaction notes

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