Azetidine → 4-[(6-(azetidin-1-yl)-5-chloropyridin-3-yl)oxy]-3-cyano-N-(5-fluoropyridin-2-yl)benzenesulfonamide

HRID 2178113Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=3)(=[O:18])=[O:17])=[CH:12][C:11]=2[C:27]#[N:28])[CH:5]=[N:6][C:7]=1F.[NH:29]1[CH2:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[N:29]1([C:7]2[N:6]=[CH:5][C:4]([O:9][C:10]3[CH:15]=[CH:14][C:13]([S:16]([NH:19][C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=4)(=[O:18])=[O:17])=[CH:12][C:11]=3[C:27]#[N:28])=[CH:3][C:2]=2[Cl:1])[CH2:32][CH2:31][CH2:30]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4-((5-chloro-6-fluoropyridin-3-yl)oxy)-3-cyano-N-(5-fluoropyridin-2-yl)benzenesulfonamide (Example 242, 200 mg, 0.47 mmol) in dimethylsulfoxide (2 mL) was added azetidine (54 mg, 0.94 mmol) followed by potassium carbonate (130 mg, 0.94 mmol) and the reaction was heated to 50° C. for 17 hours. The mixture was filtered and purified using preparative HPLC to afford the title compound.

Workup

filtrationThe mixture was filtered
custompurified

Sources & evidence

ORD record: ord-a45a1ce544154a29b072ac28d219a178
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067922B2

Reaction notes

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