1,2-Dichloroethane → HCID 178485437、化合物

HRID 491633

反応式

HRID 491633 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[NH2:19])[O:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([NH:11][CH3:12])=[O:10].[Cl:20][C:21]1[CH:34]=[CH:33][C:32]([N:35]=[C:36]=S)=[CH:31][C:22]=1[CH2:23][N:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1.C(Cl)CCl>CC#N>[Cl:20][C:21]1[CH:34]=[CH:33][C:32]([NH:35][C:36]2[NH:19][C:18]3[CH:17]=[CH:16][C:4]([O:5][C:6]4[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=4)[C:9]([NH:11][CH3:12])=[O:10])=[CH:3][C:2]=3[N:1]=2)=[CH:31][C:22]=1[CH2:23][N:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1

参加物

5

反応物 3

HCID 111,2-DichloroethaneHCID 17755843HCID 17755843、化合物HCID 690171513-(3,4-Diamino-phenoxy)-N-methyl-benzamide

生成物 1

HCID 178485437HCID 178485437、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

3-(3,4-Diamino-phenoxy)-N-methyl-benzamide (Step C, 400 mg, 1.5 mmol, 1.0 eq.) was dissolved in anh. CH3CN (10 mL) and a solution of 1-(2-chloro-5-isothiocyanato-benzyl)-4-methyl-piperazine (330 mg, 1.2 mmol, 0.8 eq.) in CH3CN (10 mL) was added dropwise. The reaction was stirred at RT for 2 h. EDC (240 mg, 1.3 mmol, 0.9 eq.) was added, the mixture was heated to 80° C. and stirred for 2 h. The CH3CN was evaporated and the crude compound was dissolved in CH2Cl2, washed with water and sat. NaHCO3 (aq.). The organic layer was dried (MgSO4), filtered and concentrated. Further purification by column chromatography (0-10% EtOH/CH2Cl2, two runs were required) gave pure 3-{2-[4-chloro-3-(4-methyl-piperazin-1-ylmethyl)-phenylamino]-1H-benzimidazol-5-yloxy}-N-methyl-benzamide. MS m/z=505.2 (M+H)+; MW Calc'd for C27H29N6O2: 504.20.

後処理

  1. temperaturethe mixture was heated to 80° C.
  2. stirringstirred for 2 h
  3. customThe CH3CN was evaporated
  4. dissolutionthe crude compound was dissolved in CH2Cl2
  5. washwashed with water and sat. NaHCO3 (aq.)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customFurther purification by column chromatography (0-10% EtOH/CH2Cl2, two runs were required)

出典と根拠

ORDレコード
ord-17a3d6edc86b4a7bb09132746d3ea342
出典データセット
uspto-grants-2009_05
特許番号
US07531553B2

関連ノート

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