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

HRID 2088655Notes

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]([C:22]#[N:23])=[CH:20][CH:19]=[C:18](Cl)[N:17]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.C(OCC)(=O)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[C:22]#[N:23]

Participants

Conditions

Temperature: 130 °C

Procedure

2.15 g (10.7 mmol) of tert-butyl 3-aminopiperidine-1-carboxylate, 1.50 g (9.77 mmol) of 2-amino-6-chloropyridine-3-carbonitrile (Example 7A) and 1.89 g (14.7 mmol) of diisopropylethylamine were suspended in 6 ml of DMSO and heated in a microwave reactor at 130° C. for 8 h. The reaction mixture was diluted with ethyl acetate (100 ml) and water (40 ml), and the organic phase was separated off and washed with saturated sodium chloride solution (50 ml), dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel (mobile phase: cyclohexane-ethyl acetate 4:1 to 1:1). This gave 2.04 g (60% of theory) of the product as a solid.

Workup

customthe organic phase was separated off
washwashed with saturated sodium chloride solution (50 ml)
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was chromatographed on silica gel (mobile phase: cyclohexane-ethyl acetate 4:1 to 1:1)

Sources & evidence

ORD record: ord-40591bd123974d3fbf473229e10bbd8a
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436003B2

Reaction notes

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