N,N-Dimethylethylenediamine → 4-Methoxy-benzo[a]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide

HRID 719188ノート

反応式

HRID 719188 の反応式
[CH3:1][O:2][C:3]1[C:8]2=[CH:9][CH:10]=[C:11]3[C:20]([N:19]=[C:18]4[C:13]([CH:14]=[CH:15][CH:16]=[C:17]4[C:21]([OH:23])=O)=[N:12]3)=[C:7]2[CH:6]=[CH:5][CH:4]=1.[C:24](N1C=CN=C1)([N:26]1[CH:30]=[CH:29][N:28]=[CH:27]1)=O.CN(C)CCN>CN(C)C=O>[CH3:24][N:26]([CH3:27])[CH2:30][CH2:29][NH:28][C:21]([C:17]1[C:18]2[C:13](=[N:12][C:11]3[C:20]([N:19]=2)=[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]2=[CH:9][CH:10]=3)[CH:14]=[CH:15][CH:16]=1)=[O:23]

参加物

5

反応物 3

HCID 66053N,N-DimethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 111202464-Methoxy-benzo[a]phenazine-11-carboxylic Acid

生成物 1

HCID 99514874-Methoxy-benzo[a]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide収率 75.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4-methoxy-benzo[a]phenazine-11-carboxylic acid (II.1) (129 mg) and 1,1′-carbonyldiimidazole (138 mg) was stirred in dry N,N-dimethylformamide (8 mL) at room temperature for 4 hours. To this mixture was added N,N-dimethylethylenediamine (commercially available)(0.5 mL) and the reaction mixture was stirred at room temperature for a further 30 minutes. The volatiles were then removed in vacuo. The residue was dissolved in dichloromethane, washed with water, dried (MgSO4) and the solvent removed in vacuo to provide crude product. This was purified using flash chromatography (5% methanol in dichloromethane) to yield the title compound as a bright yellow solid (120 mg).

後処理

  1. customThe volatiles were then removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto provide crude product
  7. customThis was purified

出典と根拠

ORDレコード
ord-06b9bb860ac248ab8255d7e537064d54
出典データセット
uspto-grants-2006_11
特許番号
US07132419B2

反応ノート

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