Water → 2-Chloro-6-(3-methoxy-1-azetidinyl)-4-[1-(3-oxetanyl)-4-piperidinyl]pyridine

HRID 1778184Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2,6-dichloro-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridine (450 mg, 1.57 mmol), 3-methoxyazetidine hydrochloride (963 mg, 7.83 mmol) and DIPEA (3 mL, 16.9 mmol) in DMSO (5 mL) was stirred at 100° C. for 16 h. The mixture was poured into water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, evaporated and purified by flash column chromatography on silica gel (30% ethyl acetate in petroleum ether) to give 2-chloro-6-(3-methoxyazetidin-1-yl)-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridine (320 mg, 60.3% yield). LCMS (ESI) [MH]+=337.8

Workup

extractionextracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
customevaporated
custompurified by flash column chromatography on silica gel (30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-5ab329c9e2f7463aadf949b8d7089685
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266862B2

Reaction notes

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