Potassium Carbonate → HCID 89761966、化合物

To a solution of 4-(2-hydroxyphenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (From Example 256, Step 3; 550 mg, 1.080 mmol) and 2-bromoacetonitrile (194 mg, 1.62 mmol) in DMF (10 mL) was added potassium carbonate (447 mg, 3.24 mmol). The reaction mixture was heated at 80° C. for 12 h. After completion, the reaction mixture was cooled to room temperature, diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with water (3×50 mL), dried over sodium sulfate and concentrated under reduced pressure to obtain the crude material which was purified by combiflash column chromatography (column size: 12 g; elution: 0-30% ethyl acetate in hexane) to yield 4-(2-(cyanomethoxy)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (200 mg, 33.8%). MS (ESI, positive ion) m/z; 549.1 (M+1)

1. temperatureAfter completion, the reaction mixture was cooled to room temperature
2. extractionextracted with ethyl acetate (2×50 mL)
3. washThe combined organic layer was washed with water (3×50 mL)
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customto obtain the crude material which
7. customwas purified by combiflash column chromatography (column size: 12 g; elution: 0-30% ethyl acetate in hexane)

ORDレコード

ord-63cd040bd98b407ab89a191b68de1a0a

出典データセット

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09346798B2