Triethylamine → 7-Bromo-N-(5-(2-(2,2-dimethylpyrrolidin-1-yl)ethylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 335292

反応式

HRID 335292 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:20]=[CH:21][C:22]=3[F:23])[C:17](O)=[O:18])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.[CH3:24][C:25]1([CH3:33])[CH2:29][CH2:28][CH2:27][N:26]1[CH2:30][CH2:31][NH2:32].C(N(CC)CC)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CCOC(C)=O.CN(C=O)C>[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:32][CH2:31][CH2:30][N:26]4[CH2:27][CH2:28][CH2:29][C:25]4([CH3:33])[CH3:24])[CH:20]=[CH:21][C:22]=3[F:23])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 451570772-(2,2-Dimethylpyrrolidin-1-yl)ethan-1-amineHCID 712834433-[(7-Bromo-imidazo[1,2-a]pyridine-3-carbonyl)-amino]-4-fluorobenzoic acid2 回

生成物 1

HCID 712834147-Bromo-N-(5-(2-(2,2-dimethylpyrrolidin-1-yl)ethylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

3-(7-Bromoimidazo[1,2-a]pyridine-3-carboxamido)-4-fluorobenzoic acid (prepared by hydrolysis of methyl 3-(7-bromoimidazo[1,2-a]pyridine-3-carboxamido)-4-fluorobenzoate (Intermediate 1A) using NaOH) (700 mg, 1.851 mmol), 2-(2,2-dimethylpyrrolidin-1-yl)ethanamine (290 mg, 2.036 mmol) and triethylamine (0.774 ml, 5.55 mmol) were dissolved in EtOAc (7.284 ml) and DMF (1.28 ml) to give a yellow solution. ®T3P (propylphosphonic anhydride) (1.620 ml, 2.036 mmol) was added and the mixture was stirred at room temperature for 90 mins. The reaction mixture was diluted with EtOAc and washed with 0.5M LiCl in H2O and sat NaHCO3. The organic portion was dried MgSO4, filtered and concentrated in vacuo. The residue was triturated with EtOAc/iso-hexane to afford the title compound as a white solid;

後処理

  1. washwashed with 0.5M LiCl in H2O
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with EtOAc/iso-hexane

出典と根拠

ORDレコード
ord-b43b35454de24913887042992d8828be
出典データセット
uspto-grants-2014_11
特許番号
US08883819B2

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