Sodium Bicarbonate → 3-[1-(3H-imidazo[4,5-b]pyridin-2-yl)-2,3-dihydro-1H-indol-5-yl]-1-(1-methylethyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 82570

反応式

HRID 82570 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:14]4=[N:15][CH:16]=[CH:17][CH:18]=[C:13]4[N:12]([CH:19]([CH3:21])[CH3:20])[C:11]3=[O:22])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl[C:24]1[NH:32][C:27]2=[N:28][CH:29]=[CH:30][CH:31]=[C:26]2[N:25]=1.C([O-])(O)=O.[Na+]>CN1C(=O)CCC1>[N:25]1[C:26]2[C:27](=[N:28][CH:29]=[CH:30][CH:31]=2)[NH:32][C:24]=1[N:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:14]4=[N:15][CH:16]=[CH:17][CH:18]=[C:13]4[N:12]([CH:19]([CH3:20])[CH3:21])[C:11]3=[O:22])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 585772553-(2,3-dihydro-1H-indol-5-yl)-1-(1-methylethyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-oneHCID 178478314HCID 178478314、化合物

生成物 1

HCID 1784565893-[1-(3H-imidazo[4,5-b]pyridin-2-yl)-2,3-dihydro-1H-indol-5-yl]-1-(1-methylethyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one収率 5.4%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
140 °C

実験手順

A mixture of 3-(2,3-dihydro-1H-indol-5-yl)-1-(1-methylethyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (200 mg) and 2-chloro-3H-imidazo[4,5-b]pyridine (115 mg) in NMP (4 mL) was stirred at 140° C. for 1.5 h, treated with saturated NaHCO3, and extracted with AcOEt. The organic layer was dried over MgSO4, passed through celite pad covered with activated carbon and concentrated in vacuo. The residue was purified by prep. HPLC. The product was crystallized from EtOH/hexane to give the title compound (15.0 mg).

後処理

  1. extractionextracted with AcOEt
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by prep
  5. customThe product was crystallized from EtOH/hexane

出典と根拠

ORDレコード
ord-774f2b9bbdce46398d50995502296235
出典データセット
uspto-grants-2014_09
特許番号
US08846713B2

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