Acetic Acid → HCID 9955653、化合物

HRID 2307389ノート

反応式

HRID 2307389 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH:13]=[CH:12][C:11]([CH3:14])=[N:10]2)[CH:6]=[CH:5][C:4]=1[C:15]([N:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:21][N:20]2[CH:28]=[CH:29][CH:30]=[C:19]2[CH2:18]1)=[O:16].C(O)(=O)C.C=O>CO>[CH3:15][N:17]([CH2:23][C:28]1[N:20]2[C:19]([CH2:18][N:17]([C:15]([C:4]3[CH:5]=[CH:6][C:7]([N:9]4[CH:13]=[CH:12][C:11]([CH3:14])=[N:10]4)=[CH:8][C:3]=3[O:2][CH3:1])=[O:16])[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21]2)=[CH:30][CH:29]=1)[CH3:18]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 712FormaldehydeHCID 10200885HCID 10200885、化合物

生成物 1

HCID 9955653HCID 9955653、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of [2-methoxy-4-(3-methyl-pyrazol-1-yl)-phenyl](5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl) methanone from Example 107 (0.57 g) in warm methanol (10 ml) was added N,N,N,N′-tetramethyl-diaminomethane (0.392 ml) and acetic acid (0.164 ml). Following the addition of aqueous 37% formalin solution (2.9 ml) the reaction was stirred for fifteen minutes. The mixture was concentrated in vacuo and partitioned between dichloromethane and sodium hydrogen carbonate. The organic phase was removed, washed with brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed in vacuo. The residue was purified by flash column chromatography on silica eluting with chloroform/methanol (50/1) to afford a solid. Recrystallisation of the solid from acetone gave the title compound as a colorless solid, m.p. 196-198° C.

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. custompartitioned between dichloromethane and sodium hydrogen carbonate
  3. customThe organic phase was removed
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe solution was filtered
  7. customthe solvent removed in vacuo
  8. customThe residue was purified by flash column chromatography on silica eluting with chloroform/methanol (50/1)
  9. customto afford a solid
  10. customRecrystallisation of the solid from acetone

出典と根拠

ORDレコード
ord-ae17bf9b730042a4b0c886719c114d86
出典データセット
uspto-grants-2004_12
特許番号
US06831079B1

反応ノート

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