Water → HCID 178458985, 화합물

HRID 549503노트

반응식

HRID 549503 반응식
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:38](=[CH:39][CH:40]=2)[C:16]2[N:17](COCC[Si](C)(C)C)[C:18]([C:20]4[C:27]([C:28]#[N:29])=[CH:26][CH:25]=[CH:24][C:21]=4[C:22]#[N:23])=[N:19][C:15]=2[C:14]2[CH:13]=[CH:12][C:11]([CH2:41][C:42]([OH:45])([CH3:44])[CH3:43])=[CH:10][C:9]3=2)[CH2:3][CH2:2]1.O>CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:38](=[CH:39][CH:40]=2)[C:16]2[NH:17][C:18]([C:20]4[C:27]([C:28]#[N:29])=[CH:26][CH:25]=[CH:24][C:21]=4[C:22]#[N:23])=[N:19][C:15]=2[C:14]2[CH:13]=[CH:12][C:11]([CH2:41][C:42]([OH:45])([CH3:43])[CH3:44])=[CH:10][C:9]3=2)[CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 962WaterHCID 86614884HCID 86614884, 화합물

생성물 1

HCID 178458985HCID 178458985, 화합물수율 36%

시약·촉매·용매 1

HCID 2724141Tetrabutylammonium Fluoride용매

실험 절차

Crude 2-(9-(cyclopropylmethoxy)-6-(2-hydroxy-2-methylpropyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-phenanthro[9,10-d]imidazol-2-yl)isophthalonitrile (1.37 mmol) from Step 6 above was dissolved in TBAF (1 M in THF, 10 mL) and the mixture heated at reflux for 1.5 h. Water was added, and the aqueous layer extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered and concentrated. The material was purified by flash chromatography on silica (70% ethyl acetate in hexanes) to afford 2-[9-(cyclopropylmethoxy)-6-(2-hydroxy-2-methylpropyl)-1H-phenanthro[9,10-d]imidazol-2-yl] isophthalonitrile (240 mg).

후처리

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1.5 h
  3. extractionthe aqueous layer extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by flash chromatography on silica (70% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-6a1aa37d2a1f4d9f8df76ffadbdbb318
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943649B2

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