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

HRID 1984599Notes

Reaction equation

HRID 1984599 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[C:4]([CH2:9][CH3:10])[N:3]=1.[N:11]1([S:17]([C:20]2[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[Cl:27][C:28]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:29]=1[S:38](Cl)(=[O:40])=[O:39]>>[Cl:27][C:28]1[CH:33]=[C:32]([C:34]([F:36])([F:35])[F:37])[CH:31]=[CH:30][C:29]=1[S:38]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:26][C:23]2[CH:22]=[CH:21][C:20]([S:17]([N:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)(=[O:19])=[O:18])=[CH:25][CH:24]=2)=[C:4]([CH2:9][CH3:10])[N:3]=1)(=[O:40])=[O:39]

Participants

4

Reactant 3

HCID 27366752-Chloro-4-(trifluoromethyl)benzenesulfonyl chlorideHCID 217103385-Bromo-6-ethylpyridin-2-amineHCID 577183134-(N-morpholinylsulfonyl)thiophenol

Product 1

HCID 577181942-Chloro-N-{6-ethyl-5-[4-(morpholine-4-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-4-trifluoromethyl-benzenesulfonamide

Procedure

Prepared from 2-amino-5-bromo-6-ethylpyridine 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): 8.41 (1H, d, J 10 Hz, A-ring CH ortho to SO2NH), 7.81-7.63 (5H, m, Ar CH's), 7.20 (2H, d, 2×C-ring CH's), 6.94 (1H, d, J 10 Hz, pyridyl CH's), 3.83-3.77 (4H, m, CH2OCH2), 3.09-2.98 (4H, m, CH2NCH2), 2.93 (3H, q, J 9 Hz, CH2CH3), 1.31 (3H, t, J 9 Hz, CH2CH3). Hplc (Luna 2, Gradient 5): rt=6.26 minutes. LC/MS rt=6.92 minutes, 622 (MH+).

Workup

  1. customrt=6.26 minutes
  2. customLC/MS rt=6.92 minutes, 622 (MH+)

Sources & evidence

ORD record
ord-2674fe47ddb348b5afd4f03c805c09b3
Source dataset
uspto-grants-2009_06
Patent number
US07544702B2

Reaction notes

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