Water → HCID 178451958, compound
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N+:3]=1[O-:12].[NH2:13][C@@H:14]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1.CCN(C(C)C)C(C)C.O>CCCCO.CN(C1C=CN=CC=1)C>[O-:12][N+:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[NH:13][C@@H:14]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
To a solution of the compound from Step 2 1-chloroisoquinoline 2-oxide (1.2 g, 6.68 mmol) and tert-butyl (3R)-3-aminopiperidine-1-carboxylate (2.0 g, 10.02 mmol) in n-BuOH (20 mL) was added DIPEA (0.95 g, 7.35 mmol) and DMAP (81 mg, 0.668 mmol). The mixture was stirred at 120° C. for 16 h. The mixture was then poured into water (20 mL) and extracted with EtOAc (3×10 mL). The combined layers organic were dried over Na2SO4, filtered, and the filtrate was concentrated in vacuo. The crude product was purified by silica gel flash column chromatography eluting with a gradient of petroleum ether: EtOAc (1:1 to 0:1) to afford the title compound (0.8 g, 35%).
Workup
- extractionextracted with EtOAc (3×10 mL)
- dry with materialThe combined layers organic were dried over Na2SO4
- filtrationfiltered
- concentrationthe filtrate was concentrated in vacuo
- customThe crude product was purified by silica gel flash column chromatography
- washeluting with a gradient of petroleum ether: EtOAc (1:1 to 0:1)
Sources & evidence
- ORD record
- ord-2c21a77887b3468f95ffbdc645d46e6e
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227956B2
Reaction notes
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