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

HRID 335269

反応式

HRID 335269 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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;

後処理

  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

出典と根拠

ORDレコード
ord-4fe692db07194191a3b9e2b5dc83a22a
出典データセット
uspto-grants-2014_11
特許番号
US08883819B2

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