tert-Butyl 4-oxopiperidine-1-carboxylate → 2-Amino-3-[(1-t-butoxycarbonylpiperidin-4-yl)amino)-6-methoxypyridine

HRID 20089

반응식

HRID 20089 반응식
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C:16]1[C:21]([NH2:22])=[CH:20][CH:19]=[C:18]([O:23][CH3:24])[N:17]=1.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][C:35](=O)[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>ClC(Cl)C>[NH2:15][C:16]1[C:21]([NH:22][CH:35]2[CH2:36][CH2:37][N:32]([C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])[CH2:33][CH2:34]2)=[CH:20][CH:19]=[C:18]([O:23][CH3:24])[N:17]=1

참가 물질

5

반응물 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 30239202,3-Diamino-6-methoxypyridineHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 222931662-Amino-3-[(1-t-butoxycarbonylpiperidin-4-yl)amino)-6-methoxypyridine

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

Sodium triacetoxyborohydride (3.39 g, 16.0 mmol) was added to a solution of 2,3-diamino-6-methoxypyridine (2.23 g, 16.0 mmol) and N-(t-butoxycarbonyl)-4-piperidone (7.66 g, 38.4 mmol) in dichloroethane (50 mL) at room temperature. The reaction was quenched with water (50 mL) and stirred overnight, then extracted with chloroform and washed with 5% aqueous sodium hydroxide, water and saturated sodium chloride solution. After drying over sodium sulfate, the solution was filtered and evaporated to give the crude product. This was purified by chromatography, where the more polar product was isolated (silica gel, 50% ethyl acetate hexane, Rf=0.36), to give the title compound. MS 323 (M+1). 1H NMR (500 MHz, CDCl3) δ 7.99 (d, J=8 Hz, 1H), 6.05 (d, J=8 Hz, 1H), 4.45 (br s), 4.03 (br s), 3.83 (s, 3H), 3.15 (m, 1H), 2.86 (m, 2H), 1.91 (d, J=12 Hz, 2H), 1.5 (br s, 11H), 1.26 (br s, 2H).

후처리

  1. customThe reaction was quenched with water (50 mL)
  2. extractionextracted with chloroform
  3. washwashed with 5% aqueous sodium hydroxide, water and saturated sodium chloride solution
  4. dry with materialAfter drying over sodium sulfate
  5. filtrationthe solution was filtered
  6. customevaporated
  7. customto give the crude product
  8. customThis was purified by chromatography, where the more polar product
  9. customwas isolated (silica gel, 50% ethyl acetate hexane, Rf=0.36)

출처 및 근거

ORD 기록
ord-d2a9a21ecf4e474e9b1c324b74675e82
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745427B2

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