1,2-Dichloroethane → HCID 178485437, compound

HRID 491633Notes

Reaction equation

HRID 491633 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 178485437HCID 178485437, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-17a3d6edc86b4a7bb09132746d3ea342
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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