2-Methylpentane → 7-Bromo-N-(2-methyl-5-(2-(4-methylpiperazin-1-yl)benzylcarbamoyl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 335269Notes

Reaction equation

HRID 335269 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=3[CH3:24])[C:17](OC)=[O:18])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.[CH3:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[CH2:38][NH2:39])[CH2:28][CH2:27]1.CCCC(C)C>C1(C)C=CC=CC=1.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:15]=[C:16]([C:17](=[O:18])[NH:39][CH2:38][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[N:29]4[CH2:28][CH2:27][N:26]([CH3:25])[CH2:31][CH2:30]4)[CH:21]=[CH:22][C:23]=3[CH3:24])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1

Participants

6

Reactant 3

HCID 78922-MethylpentaneHCID 27955682-(4-Methyl-1-piperazinyl)benzenemethanamineHCID 71283103Methyl 3-(7-bromoimidazo[1,2-a]pyridine-3-carboxamido)-4-methylbenzoate2×

Product 1

HCID 712831077-Bromo-N-(2-methyl-5-(2-(4-methylpiperazin-1-yl)benzylcarbamoyl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 3-(7-bromoimidazo[1,2-a]pyridine-3-carboxamido)-4-methylbenzoate (Intermediate 1B) (400 mg, 1.030 mmol) and TBD (143 mg, 1.030 mmol) in toluene (10 ml) was treated with (2-(4-methylpiperazin-1-yl)phenyl)methanamine (212 mg, 1.030 mmol) and heated at 100° C. under nitrogen overnight. Further TBD (106 mg, 0.82 mmol) was added the mixture was heated at 100° C. for a further 24 hrs. The solvent was removed in vacuo and the residue was partitioned between EtOAc (50 ml) and sodium bicarbonate solution (50 ml). The organic portion was separated and washed with sodium bicarbonate (2×25 ml), dried (MgSO4), filtered and evaporated to dryness to give a yellow solid. Purification by chromatography on silica eluting with 0-20% 2M NH3 in MeOH/DCM afforded a colourless oil. The oil was dissolved in minimum volume of EtOAc and titurated iso-hexane to afford the title compound as a white solid;

Workup

  1. additionFurther TBD (106 mg, 0.82 mmol) was added the mixture
  2. temperaturewas heated at 100° C. for a further 24 hrs
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between EtOAc (50 ml) and sodium bicarbonate solution (50 ml)
  5. customThe organic portion was separated
  6. washwashed with sodium bicarbonate (2×25 ml)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customto give a yellow solid
  11. customPurification by chromatography on silica eluting with 0-20% 2M NH3 in MeOH/DCM
  12. customafforded a colourless oil

Sources & evidence

ORD record
ord-4fe692db07194191a3b9e2b5dc83a22a
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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