1,1'-Carbonyldiimidazole → HCID 70161804, 화합물

HRID 1017611노트

반응식

HRID 1017611 반응식
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[CH3:13][O:14][C:15]1[CH:23]=[C:22]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=O.N[C@H:31]1[CH2:36][C:35]2[C:37]([N:41]3[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]3)=[CH:38][CH:39]=[CH:40][C:34]=2[O:33][CH2:32]1>CN(C)C=O>[CH3:47][N:44]1[CH2:45][CH2:46][N:41]([C:37]2[C:35]3[CH2:36][C@@H:31]([C:23]4[C:15]([O:14][CH3:13])=[C:16]([CH:20]=[CH:21][C:22]=4[N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[C:17]([NH2:3])=[O:19])[CH2:32][O:33][C:34]=3[CH:40]=[CH:39][CH:38]=2)[CH2:42][CH2:43]1

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 11139461(S)-3-amino-5-(4-methylpiperazin-1-yl)-1,4-dihydro-2H-1-benzopyranHCID 22064029HCID 22064029, 화합물

생성물 1

HCID 70161804HCID 70161804, 화합물수율 32.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A stirred solution of 1,1′-carbonyldiimidazole (222 mg, 1.37 mmol) and 2-methoxy-4-morpholinobenzoic acid (176 mg, 0.740 mmol) in anhydrous N,N-dimethylformamide (5 mL) was heated at 75° C. for 2 h, and was then allowed to cool. A solution of (S)-3-amino-5-(4-methylpiperazin-1-yl)-3,4-dihydro-2H-1-benzopyran (183 mg, 0.740 mmol) in anhydrous N,N-dimethylformamide (4 mL) was added. The reaction mixture was stirred at room temperature for 5 days. The solvent was removed in vacuo, and the residue was partitioned between ethyl acetate (50 mL) and a 2 M NH3 solution (15 mL). The organic layer was dried (MgSO4), and the solvent was removed in vacuo. The residue was purified by column chromatography on silica (eluent: chloroform/ethanol, 93:7+0.5% conc. NH3) affording 113 mg (30% yield) of the title compound as an uncolored foam: [α]21D−141° (c 0.5, chloroform); EIMS (70 eV) m/z (relative intensity) 466 (20, M30 ).

후처리

  1. temperatureto cool
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between ethyl acetate (50 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by column chromatography on silica (eluent: chloroform/ethanol, 93:7+0.5% conc. NH3)

출처 및 근거

ORD 기록
ord-8b87fa285074406db7457cc07df33720
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479497B1

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