Azetidine → HCID 44554097, compound

HRID 2359428Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[C:11]([C:18]([NH:20][C:21]4[S:22][CH:23]=[CH:24][N:25]=4)=[O:19])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.[NH:26]1[CH2:29][CH2:28][CH2:27]1.[F-].[Cs+].CC([O-])(C)C.[K+]>CN(C=O)C.O>[N:26]1([C:2]2[CH:7]=[C:6]([C:8]3[CH:17]=[CH:16][C:15]4[C:10](=[C:11]([C:18]([NH:20][C:21]5[S:22][CH:23]=[CH:24][N:25]=5)=[O:19])[CH:12]=[CH:13][CH:14]=4)[N:9]=3)[CH:5]=[CH:4][N:3]=2)[CH2:29][CH2:28][CH2:27]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-(2-chloropyridin-4-yl)-N-(thiazol-2-yl)quinoline-8-carboxamide (200 mg, 0.55 mmol), azetidine (314 mg, 5.5 mmol), CsF (84 mg, 0.55 mmol) and t-BuOK (185 mg, 1.65 mmol) in DMF (4 mL) under N2 was microwave heated (150° C.×12 min). The reaction mixture was cooled, diluted with water, and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel (10% methanol in CH2Cl2) to obtain of 2-(2-(azetidin-1-yl)pyridin-4-yl)-N-(thiazol-2-yl)quinoline-8-carboxamide as a solid (50 mg, 23% yield). MS (ESI) calcd for C21H17N5OS (m/z): 387.12. found: 388 [M+1].

Workup

temperatureThe reaction mixture was cooled
extractionextracted with ethyl acetate (3×10 mL)
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by chromatography on silica gel (10% methanol in CH2Cl2)

Sources & evidence

ORD record: ord-c30ec76af8eb4a1897ff8eec794e458f
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685970B2

Reaction notes

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