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

HRID 20089

反応式

HRID 20089 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d2a9a21ecf4e474e9b1c324b74675e82
出典データセット
uspto-grants-2010_06
特許番号
US07745427B2

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