O-(naphthalen-1-ylmethyl)hydroxylamine → HCID 58989906, 화합물

HRID 1663148노트

반응식

HRID 1663148 반응식
FC1C(O[C:9](=[O:24])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][CH2:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=C(F)C(F)=C(F)C=1F.[C:29]1([CH2:39][O:40][NH2:41])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[C:29]1([CH2:39][O:40][NH:41][C:9](=[O:24])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][CH2:17][C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1

참가 물질

4

반응물 2

HCID 15009996O-(naphthalen-1-ylmethyl)hydroxylamineHCID 58989934HCID 58989934, 화합물

생성물 1

HCID 58989906HCID 58989906, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

2-[(Pyridin-4-ylmethyl)-amino]-benzoic acid pentafluorophenyl ester (preparation 7C, 150 mg) and O-naphthalen-1-ylmethyl-hydroxylamine (preparation 53, 1.05 eq.) was dissolved in DMF and the stirred mixture was heated to 50° C. The reaction mixture was stirred at this temperature for 15 hours. The mixture was cooled to room temperature and partitioned between EtOAc and water. The organic layer washed with brine, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc) and gave the title compound. 13C-NMR (DMSO-d6) δ 167.3, 149.5, 149.1, 148.4, 133.2, 132.5, 131.9, 131.4, 129.3, 128.4, 128.2, 126.3, 126.1, 125.9, 125.2, 124.8, 121.9, 114.8, 113.4, 111.5, 75.3, 44.8.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between EtOAc and water
  3. washThe organic layer washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (petroleum ether/EtOAc)

출처 및 근거

ORD 기록
ord-d603c02062204037ae9215d247527a86
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08034811B2

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