4-Chloro-3-(trifluoromethyl)benzenesulfonyl Chloride → HCID 57942078, compound

HRID 418987Notes

Reaction equation

HRID 418987 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])=[N:6][CH:7]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][C:19]=1[C:28]([F:31])([F:30])[F:29]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:16][C:4]2[C:5]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[F:15])=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)(=[O:25])=[O:26])=[CH:20][C:19]=1[C:28]([F:31])([F:29])[F:30]

Participants

5

Reactant 2

HCID 27807194-Chloro-3-(trifluoromethyl)benzenesulfonyl ChlorideHCID 57942412HCID 57942412, compound

Product 1

HCID 57942078HCID 57942078, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 5-chloro-2-(2-fluoro-phenoxy)-pyridin-3-ylamine (75 mg, 0.31 mmol), 4-chloro-3-trifluoromethyl-benzenesulfonyl chloride (103 mg, 0.36 mmol), DMAP (20 mg, 0.16 mmol) in anhydrous pyridine (1 mL) was stirred at room temperature for 2 days. The reaction product was separated by preparative HPLC using acetonitrile-water solvent mixture and pure product fractions were lyophilized to provide pure product as a solid. 1H NMR (400 MHz, CDCl3) δ 8.16 (s, 1 H), 7.96 (s, 1 H), 7.89 (d, J=8.0 Hz, 1 H), 7.79 (s, 1 H), 7.62 (d, J=8.0 Hz, 1 H), 7.15-7.13 (m, 3 H), 7.00-6.96 (m, 1 H). MS m/z: 481.0 (M+H).

Workup

  1. customThe reaction product was separated by preparative HPLC
  2. customto provide pure product as a solid

Sources & evidence

ORD record
ord-9bf525dbeb9e4327955b1bfdbc46e2aa
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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