Diisopropylethylamine → Tert-butyl 3-[(6-amino-5-nitropyridin-2-yl)amino]piperidine-1-carboxylate

HRID 1182999Notes

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.[NH2:15][C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18](Cl)[N:17]=1.C(N(C(C)C)CC)(C)C>CS(C)=O>[NH2:15][C:16]1[N:17]=[C:18]([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:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23]

Participants

Conditions

Temperature: 120 °C

Procedure

500 mg (2.11 mmol) of tert-butyl 3-aminopiperidine-1-carboxylate, 772 mg (4.22 mmol) of 2-amino-6-chloro-3-nitropyridine and 1.05 ml (6.34 mmol) of diisopropylethylamine were suspended in 18 ml of DMSO and heated to 120° C. in a microwave reactor for 45 min. The reaction mixture was purified by means of preparative reversed-phase HPLC (method 13). 600 mg (81% of theory) of the product were isolated in solid form.

Workup

customThe reaction mixture was purified by means of preparative reversed-phase HPLC (method 13)
custom600 mg (81% of theory) of the product were isolated in solid form

Sources & evidence

ORD record: ord-de51b73f975a409da94f0937de201d91
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664246B2

Reaction notes

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