Diisopropylethylamine → (R)-tert-butyl 1-(5-carbamoyl-6-(4-(diethylamino)phenylamino)pyridin-2-yl)piperidin-3-ylcarbamate

HRID 2044052Notes

Reaction equation

Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][CH:13]=2)[N:3]=1.[NH:23]1[CH2:28][CH2:27][CH2:26][C@@H:25]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:24]1.CCN(C(C)C)C(C)C>CN1CCCC1=O.C(OCC)(=O)C>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([N:23]2[CH2:28][CH2:27][CH2:26][C@@H:25]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])[CH2:24]2)=[N:3][C:4]=1[NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][CH:13]=1)(=[O:7])[NH2:8]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-chloro-2-(4-(diethylamino)phenylamino)nicotinamide (1.669 g, 5.24 mmol), (R)-tert-butyl piperidin-3-ylcarbamate (1.573 g, 7.85 mmol), and DIEA (1.829 mL, 10.47 mmol) in N-methyl-2-pyrrolidinone (10 mL) was heated at 100° C. overnight. The reaction mixture was diluted with ethyl acetate, washed with satd. NaHCO3, water, and concentrated. The resulting residue was purified by MPLC (ISCO, hexane/ethyl acetate, 80 g silica gel column) to give 1.41 g (R)-tert-butyl 1-(5-carbamoyl-6-(4-(diethylamino)phenylamino)pyridin-2-yl)piperidin-3-ylcarbamate as a yellow solid. LCMS: (M+H)+=483.3.

Workup

washwashed with satd
concentrationNaHCO3, water, and concentrated
customThe resulting residue was purified by MPLC (ISCO, hexane/ethyl acetate, 80 g silica gel column)

Sources & evidence

ORD record: ord-d181b0d89b674b3a9c7410643babb2e9
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586751B2

Reaction notes

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