Cesium carbonate → 4-cyano-7-fluoro-N,N,5-trimethyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-2-carboxamide

HRID 17396

Reaction equation

Br[CH2:2][C:3]([C:5]1[C:18]([CH3:19])=[C:17]([C:20]#[N:21])[C:8]2[N:9]=[C:10]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[O:11][C:7]=2[C:6]=1[F:22])=O.[C:23]([NH2:26])(=[S:25])[CH3:24].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1>[C:20]([C:17]1[C:8]2[N:9]=[C:10]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[O:11][C:7]=2[C:6]([F:22])=[C:5]([C:3]2[N:26]=[C:23]([CH3:24])[S:25][CH:2]=2)[C:18]=1[CH3:19])#[N:21]

Participants

Conditions

Temperature: 100 °C

Procedure

Under nitrogen atmosphere, a toluene (100 ml) suspension of 6-bromoacetyl-4-cyano-7-fluoro-N,N,5-trimethyl-1,3-benzoxazole-2-carboxamide (I-128) (3.80 g, 10.3 mmol), thioacetamide (931 mg, 12.4 mmol) and cesium carbonate (4.36 g, 13.4 mmol) was stirred at 100° C. for 45 minutes. After cooling, the reaction liquid was filtered through Celite, the obtained filtrate was washed with water and saturated brine. Next, the organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica, gel column chromatography, and the eluate with n-hexane/ethyl acetate (1:1, v/v) gave the entitled compound (2.31 g, 65%) as a yellow solid.

Workup

temperatureAfter cooling
customthe reaction liquid
filtrationwas filtered through Celite
washthe obtained filtrate was washed with water and saturated brine
dry with materialNext, the organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-50945d146f144516ad8a370e03d000f9
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Linked notes

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