Water → Tert-butyl 2-(6-(3,4-dimethoxyphenylcarbamoyl)benzo[d]thiazol-2-ylamino)ethyl(methyl)carbamate

HRID 447148노트

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HRID 447148 반응식
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=3)=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:24]([O:28][C:29](=[O:35])[N:30]([CH2:32][CH2:33][NH2:34])[CH3:31])([CH3:27])([CH3:26])[CH3:25].O>CN1CCCC1=O>[CH3:23][O:22][C:16]1[CH:15]=[C:14]([NH:13][C:11]([C:9]2[CH:8]=[CH:7][C:5]3[N:6]=[C:2]([NH:34][CH2:33][CH2:32][N:30]([CH3:31])[C:29](=[O:35])[O:28][C:24]([CH3:25])([CH3:26])[CH3:27])[S:3][C:4]=3[CH:10]=2)=[O:12])[CH:19]=[CH:18][C:17]=1[O:20][CH3:21]

참가 물질

5

반응물 3

HCID 962WaterHCID 2756424N-Boc-N-methylethylenediamineHCID 672362232-bromo-N-(3,4-dimethoxyphenyl)benzo[d]thiazole-6-carboxamide

생성물 1

HCID 86654768Tert-butyl 2-(6-(3,4-dimethoxyphenylcarbamoyl)benzo[d]thiazol-2-ylamino)ethyl(methyl)carbamate

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
120 °C

실험 절차

A mixture of 2-bromo-N-(3,4-dimethoxyphenyl)benzo[d]thiazole-6-carboxamide (392.4 mg, 0.998 mmol), N-(2-aminoethyl)-N-methyl carbamic acid tert-butyl ester (193.4 mg, 1.11 mmol) and N—N-diisopropylethylamine (148.6 mg, 1.15 mmol) in 1-methyl-2-pyrrolidinone (3 mL) was stirred in a preheated oil bath at 120° C. for 4 h, then allowed to cool to room temperature, poured into water and extracted into ethyl acetate. The organic layer was washed with water, dried (sodium sulfate), filtered and concentrated in vacuo. The resulting residue was purified by gradient flash column chromatography, eluting with 70% to 80% ethyl acetate in heptane to yield tert-butyl 2-(6-(3,4-dimethoxyphenylcarbamoyl)benzo[d]thiazol-2-ylamino)ethyl(methyl)carbamate as a beige powder.

후처리

  1. temperatureto cool to room temperature
  2. extractionextracted into ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by gradient flash column chromatography
  8. washeluting with 70% to 80% ethyl acetate in heptane

출처 및 근거

ORD 기록
ord-5698f1c17520494aa0a74cbbb5156a8c
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481547B2

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