1,1'-Carbonyldiimidazole → 5-Methoxy-2-oxo-1-(1-t-butoxycarbonylpiperidin-4-yl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine

HRID 271886

반응식

HRID 271886 반응식
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][C:14]1[C:19]([NH:20][CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)=[CH:18][CH:17]=[C:16]([O:34][CH3:35])[N:15]=1>C(#N)C>[CH3:35][O:34][C:16]1[N:15]=[C:14]2[NH:13][C:1](=[O:2])[N:20]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[CH2:23][CH2:22]3)[C:19]2=[CH:18][CH:17]=1

참가 물질

4

반응물 2

HCID 682631,1'-CarbonyldiimidazoleHCID 222931662-Amino-3-[(1-t-butoxycarbonylpiperidin-4-yl)amino)-6-methoxypyridine

생성물 1

HCID 222932805-Methoxy-2-oxo-1-(1-t-butoxycarbonylpiperidin-4-yl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Carbonyldiimidazole (1.6 g, 9.8 mmol) was added to a solution of 2-amino-3-[(1-t-butoxycarbonylpiperidin-4-yl)amino]-6-methoxypyridine (1.29 g, 4.00 mmol) in acetonitrile (100 mL) at room temperature. The reaction was stirred until all the starting material was consumed. Methanol was added to the reaction and the solution stirred for several hours, then the solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate, washed with water and saturated brine, and then dried over magnesium sulfate. The crude product was purified by chromatography (silica gel, 2.5% to 5% methanol in methylene chloride gradient elution), which gave the title compound. MS 349 (M+1) 1H NMR (500 MHz, CDCl3) δ 8.50 (br s, 1H), 7.29 (d, J=8 Hz, 1H), 6.43 (d, J=8 Hz, 1H), 4.46 (m, 1H), 4.31 (br s, 2H), 3.90 (s, 3H), 2.85 (br s, 2H), 2.13 (m, 2H), 1.85 (d, J=12 Hz, 2H), 1.50 (s, 9H).

후처리

  1. customwas consumed
  2. additionMethanol was added to the reaction
  3. stirringthe solution stirred for several hours
  4. customthe solvent was evaporated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with water and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. customThe crude product was purified by chromatography (silica gel, 2.5% to 5% methanol in methylene chloride gradient elution), which

출처 및 근거

ORD 기록
ord-0be740d13e324469be16d45c23dd20a8
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452903B2

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