1,1'-Carbonyldiimidazole → HCID 70161804、化合物

HRID 1017611ノート

反応式

HRID 1017611 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 70161804HCID 70161804、化合物収率 32.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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 ).

後処理

  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)

出典と根拠

ORDレコード
ord-8b87fa285074406db7457cc07df33720
出典データセット
uspto-grants-2002_11
特許番号
US06479497B1

反応ノート

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