Phenylacetyl chloride → HCID 9936473, compound

HRID 1268752Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21](=O)[O:22]C(C)(C)C)[N:15]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[CH:8]=2)[N:6]=1.[C:28]1([CH2:34][C:35](Cl)=[O:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[CH3:13][C:9]1[CH:8]=[C:7]([C:5]2[N:6]=[C:2]([NH:1][C:35](=[O:36])[CH2:34][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[S:3][C:4]=2[C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21](=[O:22])[CH2:5][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:15]=2)[CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of tert-butyl 4-[2-amino-4-(3-methylphenyl)-1,3-thiazol-5-yl]-2-pyrimidinylcarbamate (0.50 g, 1.3 mmol) in N,N-dimethylacetamide (5 mL) was added phenylacetylchloride (0.52 mL, 3.9 mmol) and the mixture was stirred at 80° C. for 14 hrs. Into the reaction mixture was poured aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate=7:3), and the obtained oil was recrystallized from ethyl ether to give the title compound (0.09 g, yield 13%).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
customdried
concentrationconcentrated
customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate=7:3)
customthe obtained oil was recrystallized from ethyl ether

Sources & evidence

ORD record: ord-314f66df1b5b477f9e016e629bdfd151
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199124B2

Reaction notes

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