Diisopropylethylamine → tert-Butyl 3-({6-[(tert-butoxycarbonyl)amino]-5-propanoylpyridin-2-yl}amino)piperidine-1-carboxylate
Reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[C:15]([O:19][C:20](=[O:33])[NH:21][C:22]1[C:27]([C:28](=[O:31])[CH2:29][CH3:30])=[CH:26][CH:25]=[C:24](Cl)[N:23]=1)([CH3:18])([CH3:17])[CH3:16].C(N(C(C)C)CC)(C)C>CS(C)=O.C(OCC)(=O)C>[C:15]([O:19][C:20]([NH:21][C:22]1[N:23]=[C:24]([NH:1][CH:2]2[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]2)[CH:25]=[CH:26][C:27]=1[C:28](=[O:31])[CH2:29][CH3:30])=[O:33])([CH3:18])([CH3:17])[CH3:16]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
610 mg (3.0 mmol) of tert-butyl 3-aminopiperidine-1-carboxylate, 700 mg (2.3 mmol) of tert-butyl(6-chloro-3-propanoylpyridin-2-yl)carbamate (Example 23A) and 610 μl (3.5 mmol) of diisopropylethylamine were suspended in 7 ml of DMSO and heated in a microwave reactor at 90° C. for 45 min. The reaction mixture was diluted with ethyl acetate (100 ml) and washed with saturated aqueous ammonium chloride solution (3×40 ml), then with saturated aqueous sodium bicarbonate solution (40 ml), and the organic phase was dried over magnesium sulfate, diluted and concentrated. The residue was chromatographed on silica gel (mobile phase: cyclohexane-ethyl acetate 5:1 to 1:1). This gave 380 mg (35% of theory) of the product.
Workup
- washwashed with saturated aqueous ammonium chloride solution (3×40 ml)
- dry with materialwith saturated aqueous sodium bicarbonate solution (40 ml), and the organic phase was dried over magnesium sulfate
- additiondiluted
- concentrationconcentrated
- customThe residue was chromatographed on silica gel (mobile phase: cyclohexane-ethyl acetate 5:1 to 1:1)
Sources & evidence
- ORD record
- ord-c7f8d64b26514ea38627e8d71478701f
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08436003B2
Reaction notes
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