2-Chloro-4-(trifluoromethyl)benzenesulfonyl chloride → 2-Chloro-N-{5-[4-(morpholine-4-sulfonyl)-phenylsulfanyl]-6-trifluoromethyl-pyridin-2-yl}-4-trifluoromethyl-benzenesulfonamide

HRID 1984601Notes

Reaction equation

HRID 1984601 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1.[N:13]1([S:19]([C:22]2[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[Cl:29][C:30]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:31]=1[S:40](Cl)(=[O:42])=[O:41]>>[Cl:29][C:30]1[CH:35]=[C:34]([C:36]([F:38])([F:37])[F:39])[CH:33]=[CH:32][C:31]=1[S:40]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:28][C:25]2[CH:24]=[CH:23][C:22]([S:19]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)(=[O:21])=[O:20])=[CH:27][CH:26]=2)=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1)(=[O:42])=[O:41]

Participants

4

Reactant 3

HCID 27366752-Chloro-4-(trifluoromethyl)benzenesulfonyl chlorideHCID 457897905-Bromo-6-(trifluoromethyl)pyridin-2-amineHCID 577183134-(N-morpholinylsulfonyl)thiophenol

Product 1

HCID 577182362-Chloro-N-{5-[4-(morpholine-4-sulfonyl)-phenylsulfanyl]-6-trifluoromethyl-pyridin-2-yl}-4-trifluoromethyl-benzenesulfonamide

Procedure

Prepared from 2-amino-5-bromo-6-trifluoromethylpyridine and 4-(N-morpholinylsulfonyl)thiophenol according to General Method 11 step 1 followed by reaction with 2-chloro-4-trifluoromethylphenylsulfonyl chloride according to General Method 11 step 2. 1H NMR (CDCl3): 8.31 (1H, d, J 10 Hz, A-ring CH ortho to SO2NH), 7.45 (1H, s, A ring CH ortho to CF3 & Cl), 7.65-7.50 & 7.26-7.15 (4H & 3H, 2×m, Ar CH's), 3.71-3.61 (4H, m, CH2OCH2), 2.95-2.86 (4H, m, CH2NCH2). Hplc (Luna 2, Gradient 5): rt=6.53 minutes. LC/MS rt=7.06 minutes, 662 (MH+).

Workup

  1. customrt=6.53 minutes
  2. customLC/MS rt=7.06 minutes, 662 (MH+)

Sources & evidence

ORD record
ord-866c7a508e0c459c89ec0b7058708fff
Source dataset
uspto-grants-2009_06
Patent number
US07544702B2

Reaction notes

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