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

HRID 501086

Reaction equation

HRID 501086 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-bd03c9dca92c429db47b020c645ee15a
Source dataset
uspto-grants-2010_08
Patent number
US07772224B2

Linked notes

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