Isopropanol → Methyl 3-(3-{2-[(3-{[2-(dimethylamino)ethyl]oxy}-2-methylphenyl)amino]-4-pyrimidinyl}imidazo[1,2-a]pyridin-2-yl)benzoate

HRID 419323ノート

反応式

HRID 419323 の反応式
Cl[C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]3=[N:10][C:9]=2[C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=2)[C:20]([O:22][CH3:23])=[O:21])[CH:5]=[CH:4][N:3]=1.[NH2:27][C:28]1[C:29]([CH3:39])=[C:30]([O:34][CH2:35][CH2:36][NH:37][CH3:38])[CH:31]=[CH:32][CH:33]=1.[CH3:40]C(O)C>Cl.C(Cl)Cl>[CH3:38][N:37]([CH3:40])[CH2:36][CH2:35][O:34][C:30]1[C:29]([CH3:39])=[C:28]([NH:27][C:2]2[N:7]=[C:6]([C:8]3[N:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]4=[N:10][C:9]=3[C:17]3[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=3)[C:20]([O:22][CH3:23])=[O:21])[CH:5]=[CH:4][N:3]=2)[CH:33]=[CH:32][CH:31]=1

参加物

6

反応物 3

HCID 3776IsopropanolHCID 59452862Methyl 3-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]benzoateHCID 66649996{2-[(3-Amino-2-methylphenyl)oxy]ethyl}methylamine

生成物 1

HCID 59452717Methyl 3-(3-{2-[(3-{[2-(dimethylamino)ethyl]oxy}-2-methylphenyl)amino]-4-pyrimidinyl}imidazo[1,2-a]pyridin-2-yl)benzoate収率 68%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid触媒HCID 6344Dichloromethane溶媒

反応条件

温度
140 °C

実験手順

A microwave vial was charged with methyl 3-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]benzoate (Intermediate Example 3) (1.75 g, 4.79 mmol), {2-[(3-amino-2-methylphenyl)oxy]ethyl}methylamine (863 mg, 4.79 mmol), iPrOH (10 mL) and 1 drop HCl, and the reaction mixture was stirred in a microwave reactor at 140° C. for 30 min. The mixture was diluted with DCM and quenched with saturated NaHCO3. The organics were separated, dried over MgSO4, and the solvent was removed. The crude material was purified via silica gel chromatography to give 1.70 g (68% yield) of the title compound. MS (APCI+) m/z 523 [M+H].

後処理

  1. customquenched with saturated NaHCO3
  2. customThe organics were separated
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed
  5. customThe crude material was purified via silica gel chromatography

出典と根拠

ORDレコード
ord-cba4ee697e50470aa00d2a523bc7306c
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

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