Water → 1,2,3,9-tetrahydro-9-methyl-3-[[5-methyl(triphenylmethyl)-1H-imidazol-4-yl]methyl]carbazol-4-one

HRID 621200

반응식

HRID 621200 반응식
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][N:22]1[C:34]2[CH2:33][CH2:32][CH:31]([CH2:35][C:36]3[N:37]=[CH:38][NH:39][C:40]=3[CH3:41])[C:30](=[O:42])[C:29]=2[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2.C(N(CC)CC)C.O>CN(C=O)C>[CH3:21][N:22]1[C:34]2[CH2:33][CH2:32][CH:31]([CH2:35][C:36]3[N:37]=[CH:38][N:39]([C:7]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:40]=3[CH3:41])[C:30](=[O:42])[C:29]=2[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2

참가 물질

6

반응물 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 172316GR 67330

생성물 1

HCID 142339301,2,3,9-tetrahydro-9-methyl-3-[[5-methyl(triphenylmethyl)-1H-imidazol-4-yl]methyl]carbazol-4-one수율 57%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of triphenylchloromethane (286 mg) in dry DMF (10 ml) was added dropwise to a stirred solution of 1,2,3,9-tetrahydro-9-methyl-3-[(5-methyl-1H-imidazol-4-yl)methyl]-4H-carbazol-4-one (292 mg) and triethylamine (101 mg) in dry DMF (20 ml) and the resulting solution was stirred at room temperature under nitrogen for 3.5 h. The reaction mixture was then poured into water (100 ml) and the resultant suspension was extracted with dichloromethane (3×50 ml). The combined, dried organic extracts were adsorbed onto FCC silica which was then applied to a column and FCC eluting with System A (150:8:1) gave a solid which was further purified by crystallisation from dichloromethane:hexane (2:1) to give the title compound (304 mg), m.p. 193°-195°.

후처리

  1. extractionthe resultant suspension was extracted with dichloromethane (3×50 ml)
  2. washeluting with System A (150:8:1)
  3. customgave a solid which
  4. customwas further purified by crystallisation from dichloromethane:hexane (2:1)

출처 및 근거

ORD 기록
ord-4e3771d0851b4b57a2238a9b93786062
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04822881

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