Water → (S)-N-(1-{4-[1-(6-Chloro-pyrimidin-4-yl)-piperidin-4-yl]-phenyl}-ethyl)-acetamide

HRID 1470726Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][C:18]([C@@H:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1.O>C1COCC1>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]3[CH:20]=[CH:19][C:18]([C@@H:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

0.34 mL (2.43 mmol) TEA are added to a mixture of 181 mg (1.22 mmol) 4,6-dichloropyrimidine and 300 mg (1.22 mmol) (S)-N-[1-(4-piperidin-4-yl-phenyl)-ethyl]-acetamide (V.1) in 3 mL THF. The mixture is stirred for 5 min at 80° C. and for 2 h at rt. After that time, water is added and the mixture is extracted with dichloromethane (2×). The combined organic layers are dried over sodium sulphate. The solvent is evaporated and the residue is purified by column chromatography (silica gel; dichloromethane/methanol, gradient 98:2-95:5) to yield the desired product.

Workup

extractionthe mixture is extracted with dichloromethane (2×)
dry with materialThe combined organic layers are dried over sodium sulphate
customThe solvent is evaporated
customthe residue is purified by column chromatography (silica gel; dichloromethane/methanol, gradient 98:2-95:5)

Sources & evidence

ORD record: ord-1b8266295767487cb3c87cefc9bc87cc
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006450B2

Reaction notes

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