5-(3-chlorophenyl)-alpha-(4-fluorophenyl)-4,5-dihydro-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanol → 9-(3-chlorophenyl)-alpha-(4-fluorophenyl)-4,9-dihydro-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[5,1-b]quinazoline-7-methanol

HRID 1441476노트

반응식

HRID 1441476 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)([C:20]4[N:24]([CH3:25])[CH:23]=[N:22][CH:21]=4)[OH:19])[CH:16]=3)[N:11]3[N:33]=[N:34][N:35]=[C:10]3[NH:9]2)[CH:5]=[CH:6][CH:7]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[CH:16]=[C:15]([C:18]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)([C:20]4[N:24]([CH3:25])[CH:23]=[N:22][CH:21]=4)[OH:19])[CH:14]=[CH:13][C:12]=3[NH:11][C:10]3=[N:35][N:34]=[N:33][N:9]23)[CH:5]=[CH:6][CH:7]=1

참가 물질

3

반응물 1

HCID 1363420815-(3-chlorophenyl)-alpha-(4-fluorophenyl)-4,5-dihydro-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanol

생성물 1

HCID 1354245029-(3-chlorophenyl)-alpha-(4-fluorophenyl)-4,9-dihydro-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[5,1-b]quinazoline-7-methanol수율 51.2%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of intermediate 9 (0.0014 mol) in toluene (10 ml) was stirred and refluxed for 48 hours, then brought to room temperature and the solvent was evaporated till dryness. The residue was taken up in DCM. The solvent was evaporated till dryness. The residue was purified by column chromatography over kromasil® (10 μm) (eluent: DCM/MeOH/Et3N 95/5/0.5). The pure fractions were collected and the solvent was evaporated. The residue (0.4 g, 57%) was washed with diethyl ether. The precipitate was filtered off and dried under a vacuo, yielding 0.35 g (50%) of 9-(3-chlorophenyl)-α-(4-fluorophenyl)4,9-dihydro-α-(1-methyl-1H-imidazol-5-yl)-tetrazolo[5,1-b]quinazoline-7-methanol (compound 2), mp. 180° C.

후처리

  1. temperaturerefluxed for 48 hours
  2. custombrought to room temperature
  3. customthe solvent was evaporated till dryness
  4. customThe solvent was evaporated till dryness
  5. customThe residue was purified by column chromatography over kromasil® (10 μm) (eluent: DCM/MeOH/Et3N 95/5/0.5)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated
  8. washThe residue (0.4 g, 57%) was washed with diethyl ether
  9. filtrationThe precipitate was filtered off
  10. customdried under a vacuo

출처 및 근거

ORD 기록
ord-2f9e5b521c39433ebdfe668587099298
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07655654B2

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