Benzenesulfonyl chloride, 2,4-dichloro- → 2,4-Dichloro-N-{5-[4-(morpholine-4-sulfonyl)-phenylsulfanyl]-6-trifluoromethyl-pyridin-2-yl}-benzenesulfonamide

HRID 1366849Notes

Reaction equation

HRID 1366849 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]([Cl:36])[CH:33]=[CH:32][C:31]=1[S:37](Cl)(=[O:39])=[O:38]>>[Cl:29][C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=1[S:37]([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:39])=[O:38]

Participants

4

Reactant 3

HCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 457897905-Bromo-6-(trifluoromethyl)pyridin-2-amineHCID 577183134-(N-morpholinylsulfonyl)thiophenol

Product 1

HCID 577182782,4-Dichloro-N-{5-[4-(morpholine-4-sulfonyl)-phenylsulfanyl]-6-trifluoromethyl-pyridin-2-yl}-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 2,4-dichlorophenylsulfonyl chloride according to General Method 11 step 2. 1H NMR (CDCl3): 8.10 (1 H, d, J 10 Hz, A-ring CH ortho to SO2NH), 7.62 & 7.35 (2×1 H, 2×d, 2×J 10 Hz, pyridyl CH's), 7.56 & 7.18 (2×2 H, 2×d, 2×J 10 Hz, C-ring CH's), 7.45 (1 H, s, A ring CH ortho to 2×Cl), 7.20 (1 H, d, J 10 Hz, A-ring CH ortho to Cl), 3.71-3.63 (4H, m, CH2OCH2), 2.93-2.85 (4H, m, CH2NCH2). Hplc (Luna 2, Gradient 5): rt=6.39 minutes. LC/MS rt=7.06 minutes, 628/630 (MH+).

Workup

  1. customrt=6.39 minutes
  2. customLC/MS rt=7.06 minutes, 628/630 (MH+)

Sources & evidence

ORD record
ord-fa2608b26a354787ab8839a0571f6977
Source dataset
uspto-grants-2011_02
Patent number
US07893077B2

Reaction notes

Loading…