1,2-Dichloroethane → HCID 178485437, 화합물

HRID 491633

반응식

HRID 491633 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 178485437HCID 178485437, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-17a3d6edc86b4a7bb09132746d3ea342
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531553B2

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