4-Chloro-3-(trifluoromethyl)benzenesulfonyl Chloride → HCID 59135297, compound

HRID 387488Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([C:8]2[CH:24]=[CH:23][C:11]([O:12][C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH:21][CH3:22])=[O:20])[CH:14]=3)=[CH:10][CH:9]=2)[N:7]=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][C:27]=1[C:36]([F:39])([F:38])[F:37]>N1C=CC=CC=1>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:1][C:2]2[N:3]=[N:4][CH:5]=[C:6]([C:8]3[CH:9]=[CH:10][C:11]([O:12][C:13]4[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH:21][CH3:22])=[O:20])[CH:14]=4)=[CH:23][CH:24]=3)[N:7]=2)(=[O:33])=[O:34])=[CH:28][C:27]=1[C:36]([F:39])([F:37])[F:38]

Participants

Conditions

Temperature: 100 °C

Procedure

108.6 mg (0.337 mmol, 1.0 equivalent) of 4-[4-(3-amino-[1,2,4]triazin-5-yl)-phenoxy]-N-methylpyridine-2-carboxamide can be dissolved in 2 mL of anhydrous pyridine with heating to about 100° C. 0.405 mmol (1.2 equivalent) of 4-chloro-3-trifluoromethyl-benzenesulfonyl chloride can be added. The reaction mixture can be allowed to stir at ambient temperature for 1-2 hours. The product can be isolated by a number of methods known to one skilled in the art, such as precipitation or by extraction with a number of solvents, such as ethyl acetate, methylene chloride or diethyl ether or by silica gel column chromatography, or by reverse-phase preparative HPLC.

Workup

customThe product can be isolated by a number of methods
customknown to one skilled in the art, such as precipitation or by extraction with a number of solvents, such as ethyl acetate, methylene chloride or diethyl ether or by silica gel column chromatography

Sources & evidence

ORD record: ord-127b7098739e4f4cbec0a5a0f540e1b9
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372971B2

Reaction notes

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