Diisopropylethylamine → tert-Butyl 3-({6-[(tert-butoxycarbonyl)amino]-5-(trifluoroacetyl)pyridin-2-yl}amino)piperidine-1-carboxylate

HRID 57692

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.Cl[C:16]1[N:21]=[C:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([C:30](=[O:35])[C:31]([F:34])([F:33])[F:32])=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.C(OCC)(=O)C>[C:25]([O:24][C:23]([NH:22][C:20]1[N:21]=[C:16]([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:17]=[CH:18][C:19]=1[C:30](=[O:35])[C:31]([F:32])([F:33])[F:34])=[O:29])([CH3:28])([CH3:26])[CH3:27]

Participants

Conditions

Temperature: 90 °C

Procedure

561 mg (2.8 mmol) of tert-butyl 3-aminopiperidine-1-carboxylate, 700 mg (2.16 mmol) of tert-butyl [6-chloro-3-(trifluoroacetyl)pyridin-2-yl]carbamate (Example 32A) and 0.56 ml (3.23 mmol) of diisopropylethylamine were suspended in 14 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 (three times 40 ml) and then saturated aqueous sodium bicarbonate solution (40 ml). The organic phase was dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1 to 1:1). This gave 670 mg (63% of theory) of the product.

Workup

washwashed with saturated aqueous ammonium chloride solution (three times 40 ml)
dry with materialThe organic phase was dried over magnesium sulfate
concentrationconcentrated
customThe residue was chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1 to 1:1)

Sources & evidence

ORD record: ord-29e8997d475147c58d94b2780b9537e0
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434731B2

Linked notes

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