3-Amino-4-bromo-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamide → N-(2-Bromo-5-(2-(4-methylpiperazin-1-yl)benzylcarbamoyl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 335284Notes

Reaction equation

HRID 335284 reaction equation
Cl.[N:2]1[CH:3]=[C:4]([C:11](Cl)=[O:12])[N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12.[NH2:14][C:15]1[CH:16]=[C:17]([CH:35]=[CH:36][C:37]=1[Br:38])[C:18]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]1)=[O:19]>N1C=CC=CC=1>[Br:38][C:37]1[CH:36]=[CH:35][C:17]([C:18](=[O:19])[NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:28]2[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]2)=[CH:16][C:15]=1[NH:14][C:11]([C:4]1[N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]2=[N:2][CH:3]=1)=[O:12]

Participants

4

Reactant 2

HCID 866956773-Amino-4-bromo-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamideHCID 86695679Imidazo[1,2-a]pyridine-3-carbonyl chloride hydrochloride

Product 1

HCID 71283407N-(2-Bromo-5-(2-(4-methylpiperazin-1-yl)benzylcarbamoyl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Imidazo[1,2-a]pyridine-3-carbonyl chloride hydrochloride (0.97 mg, 4.46 mmol) was slowly added in portions to a stirred solution of 3-amino-4-bromo-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamide (step 1) (900 mg, 2.23 mmol) in dry pyridine (15 ml). The reaction was stirred at RT for 18 hrs and quenched with water. The solvent removed in vacuo. The residue was treated with a small amount of MeOH to dissolve insoluble material then partitioned between aq. NaHCO3 and DCM. The organic extract was washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product mixture was crystallised from MeOH to give a white solid;

Workup

  1. customquenched with water
  2. customThe solvent removed in vacuo
  3. additionThe residue was treated with a small amount of MeOH
  4. dissolutionto dissolve insoluble material
  5. customthen partitioned between aq. NaHCO3 and DCM
  6. extractionThe organic extract
  7. washwas washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe crude product mixture was crystallised from MeOH
  11. customto give a white solid

Sources & evidence

ORD record
ord-965d7e547a7d4df493836fa1aca07ca9
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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