2-Chloro-4-(trifluoromethyl)benzenesulfonyl chloride → HCID 57718182, compound

HRID 1366863Notes

Reaction equation

HRID 1366863 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:24])[N:5]=[N:6][C:7]=1[S:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1.[Cl:25][C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:27]=1[S:36](Cl)(=[O:38])=[O:37]>N1C=CC=CC=1>[Cl:25][C:26]1[CH:31]=[C:30]([C:32]([F:34])([F:33])[F:35])[CH:29]=[CH:28][C:27]=1[S:36]([NH:24][C:4]1[N:5]=[N:6][C:7]([S:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)(=[O:16])=[O:17])=[CH:11][CH:10]=2)=[C:2]([CH3:1])[CH:3]=1)(=[O:38])=[O:37]

Participants

4

Reactant 2

HCID 27366752-Chloro-4-(trifluoromethyl)benzenesulfonyl chlorideHCID 57718211HCID 57718211, compound

Product 1

HCID 57718182HCID 57718182, compoundYield 10.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Methyl-6-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridazin-3-ylamine (110 mgs), 2-chloro-4-trifluoromethylbenzenesulfonyl chloride (160 mgs) and pyridine (1 ml) were heated at 50° C. under nitrogen for 72 hours. All volatiles were removed and the residue purified by Preparative HPLC to give 2-chloro-N-{5-methyl-6-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridazin-3-yl}-4-trifluoromethyl-benzenesulfonamide 20 mg. 1H NMR (CDCl3) 8.25 (1H, d) 7.75 (2H, m) 7.7 (1H, s) 7.6 (3H, m) 6.95 (1H, s) 3.0 (4H, m) 2.3 (3H, s) 1.6 (4H, m) 1.45 (2H, m). LCMS Polarity/Scan type: Negative Q1 Scan. M.wt. 605 (—H), 607 (—H). Retention time 7.05 minutes. HPLC:—MS8. Retention time 4.99 minutes.

Workup

  1. customAll volatiles were removed
  2. customthe residue purified by Preparative HPLC

Sources & evidence

ORD record
ord-ce005d0950dd4c988115e0b6a115d761
Source dataset
uspto-grants-2011_02
Patent number
US07893077B2

Reaction notes

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