Diisopropylethylamine → 3-((4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)pyridin-2-yl)amino)-N-methylbenzamide

HRID 522917Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([NH:14][CH3:15])=[O:13])[CH:3]=1.CCN(C(C)C)C(C)C.[F:28][C:29]1[CH:39]=[C:38]([Cl:40])[CH:37]=[CH:36][C:30]=1[O:31][CH:32]1[CH2:35][NH:34][CH2:33]1>C(O)(C)C>[Cl:40][C:38]1[CH:37]=[CH:36][C:30]([O:31][CH:32]2[CH2:35][N:34]([C:2]3[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]4[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=4)[C:12]([NH:14][CH3:15])=[O:13])[CH:3]=3)[CH2:33]2)=[C:29]([F:28])[CH:39]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-((4-chloropyridin-2-yl)amino)-N-methylbenzamide (0.300 g, 1.14 mmol) in Isopropanol (4 mL) was added DIPEA (0.3 mL, 1.71 mmol) and 3-(2-fluoro-4-chlorophenoxy)azetidine (0.230 g, 1.14 mmol) [prepared as described in Example AAA] and the reaction mixture was heated at 80° C. for 7 h. The mixture was concentrated under reduced pressure and extracted with EtOAc (2×20 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 3-((4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)pyridin-2-yl)amino)-N-methylbenzamide (0.10 g, 3%) as a solid. Observed mass (M+1): 427.1

Workup

concentrationThe mixture was concentrated under reduced pressure
extractionextracted with EtOAc (2×20 mL)
washThe organic extracts were washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customPurification by silica gel column chromatography

Sources & evidence

ORD record: ord-50f190314309443c9d57c8c295b86515
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334269B2

Reaction notes

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