Dimethylformamide → HCID 86705028、化合物

Oxalyl chloride (0.70 g, 0.48 ml, 5.58 mmol) was added drop wise at 0° C. to a solution of 5-(4-chlorophenyl)-3-(4-sulfamoylphenyl)thiophene-2-carboxylic acid (compound 33c, 1.10 g, 2.79 mmol) in a mixture of dichloromethane (30 ml) and DMF (0.40 g, 0.43 ml, 5.58 mmol). The mixture was then allowed to warm to room temperature and stirred for 1.5 hr under a nitrogen atmosphere. The progress of the reaction was monitored by TLC. The reaction mixture was then concentrated under reduced pressure. The residue so obtained was dissolved in dry dichloromethane (30 ml) and the mixture was then cooled to 0° C. To the cooled mixture was added triethylamine (1.69 g, 2.32 ml, 16.75 mmol) followed by the addition of N, O-dimethylhydroxylamine hydrochloride (0.54 g, 5.58 mmol) under stirring. The reaction mixture was then stirred at room temperature for 2 hr. The progress of the reaction was monitored by TLC. The reaction mixture was then diluted with DCM (25 ml) and washed with water (2×25 ml) and organic layer so obtained was dried over anhydrous sodium sulphate, and concentrated under reduced pressure to obtain a crude product. The crude product was then purified by flash column chromatography using 0.8% methanol in DCM as an eluent to obtain the title compound (0.9 g, 65.69%).

1. concentrationThe reaction mixture was then concentrated under reduced pressure
2. customThe residue so obtained
3. temperaturethe mixture was then cooled to 0° C
4. stirringunder stirring
5. stirringThe reaction mixture was then stirred at room temperature for 2 hr
6. washwashed with water (2×25 ml) and organic layer
7. customso obtained
8. dry with materialwas dried over anhydrous sodium sulphate
9. concentrationconcentrated under reduced pressure
10. customto obtain a crude product
11. customThe crude product was then purified by flash column chromatography

ORDレコード

ord-f4b8a1f7622c473180638d034ecbf647

出典データセット

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09393247B2