Water → tert-butyl 4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)-4-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)piperidine-1-carboxylate

HRID 1897959Notes

Reaction equation

HRID 1897959 reaction equation
[C:1]([N:5]1[C:9]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][C:18]3([C:31]([NH:33][NH2:34])=[O:32])[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)[CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[C:35](N1C=CN=C1)(N1C=CN=C1)=[O:36].C(=O)(O)[O-].[Na+].O>O1CCCC1>[C:1]([N:5]1[C:9]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][C:18]3([C:31]4[O:32][C:35](=[O:36])[NH:34][N:33]=4)[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:20][CH2:19]3)[CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=[N:6]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-Carbonyldiimidazole2×HCID 516892Sodium BicarbonateHCID 66889292tert-butyl 4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)-4-(hydrazinocarbonyl)piperidine-1-carboxylate

Product 1

HCID 66889439tert-butyl 4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)-4-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 378 mg of tert-butyl 4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)-4-(hydrazinocarbonyl)piperidine-1-carboxylate in 10 ml of tetrahydrofuran was added 130 mg of 1,1′-carbonyldiimidazole at room temperature. After stirring at room temperature for 3 hours, 100 mg of 1,1′-carbonyldiimidazole was added at room temperature, followed by stirring at room temperature for 5 days. To the reaction mixture was added 10 ml of saturated aqueous sodium bicarbonate solution, followed by stirring the reaction mixture at room temperature for 30 minutes. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate solution was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=20/1−1/2) to give the title compound as a pale yellow oil.

Workup

  1. stirringby stirring at room temperature for 5 days
  2. stirringby stirring the reaction mixture at room temperature for 30 minutes
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate solution was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=20/1−1/2)

Sources & evidence

ORD record
ord-6f609748dd0b4aaaaa49409a4f64081f
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

Loading…