Cesium carbonate → 2-(Dimethylamino)-7-fluoro-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile

HRID 17441

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

6-(Bromoacetyl)-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-170) (0.60 g, 1.76 mmol) was dissolved in toluene (30 ml), then thioacetamide (0.16 g, 2.13 mmol) and cesium carbonate (0.75 g, 2.30 mmol) were added, followed by stirring at an external temperature of 100° C. for 16 hours. The reaction liquid was diluted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:1) to obtain a yellow solid (0.44 g, 79%).

Workup

customThe reaction liquid
washwashed with water
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated away under reduced pressure
customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:1)

Sources & evidence

ORD record: ord-9ec769c0139b4e329d8195eb0943cdaf
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Linked notes

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