Tetraethylammonium fluoride hydrate → 7-(4-Hydroxybutoxy)-8-methoxy-3-(3-methoxy-4-nitrophenyl)-5,10-dihydro-11h-dibenzo[b,e][1,4]diazepin-11-one

HRID 272716

반응식

HRID 272716 반응식
C([Si](C)(C)[O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[C:38]([O:39][CH3:40])=[CH:37][C:15]2[NH:16][C:17](=[O:36])[C:18]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[C:27]([O:34][CH3:35])[CH:26]=4)=[CH:21][C:19]=3[NH:20][C:14]=2[CH:13]=1)(C)(C)C.[N+](CC)(CC)(CC)CC.[F-].O>C1COCC1>[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[C:38]([O:39][CH3:40])=[CH:37][C:15]2[NH:16][C:17](=[O:36])[C:18]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[C:27]([O:34][CH3:35])[CH:26]=4)=[CH:21][C:19]=3[NH:20][C:14]=2[CH:13]=1

참가 물질

4

반응물 2

HCID 16211652Tetraethylammonium fluoride hydrateHCID 692189867-[4-(Tert-butyl-dimethyl-silanyloxy)-butoxy]-8-methoxy-3-(3-methoxy-4-nitro-phenyl)-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one

생성물 1

HCID 444531387-(4-Hydroxybutoxy)-8-methoxy-3-(3-methoxy-4-nitrophenyl)-5,10-dihydro-11h-dibenzo[b,e][1,4]diazepin-11-one수율 28%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of Example 500A, Et4NF.H2O (10 equiv.) and THF was heated overnight at 65° C., concentrated under vacuum, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered and concentrated under vacuum. The residue was purified by preparative HPLC to provide 50 mg (28%) of the desired product. MS (ESI) m/e 480 (M+H)+; 1H NMR (400 MHz, DMSO-d6) □ 9.63 (s, 1H), 8.01 (d, J=8.6 Hz, 1H), 7.78 (d, J=8.3 Hz, 1H), 7.71 (s, 1H), 7.53 (d, J=1.2 Hz, 1H), 7.35 (dd, J=1.5, 8.6 Hz, 1H), 7.28-7.30 (m, 2H), 6.70 (s, 1H), 6.65 (s, 1H), 4.03 (s, 3H), 3.89 (t, J=6.6 Hz, 2H), 3.67 (s, 3H), 3.44 (t, J=6.4 Hz, 2H), 1.69-1.76 (m, 2H), 1.51-1.58 (m, 2H).

후처리

  1. concentrationconcentrated under vacuum
  2. additiondiluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-1b38afa59031419398c964c659393427
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456169B2

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