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

HRID 419323노트

반응식

HRID 419323 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 6344Dichloromethane용매

반응 조건

온도
140 °C

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-cba4ee697e50470aa00d2a523bc7306c
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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