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

HRID 1366847Notes

Reaction equation

HRID 1366847 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]([Cl:34])[CH:31]=[CH:30][C:29]=1[S:35](Cl)(=[O:37])=[O:36]>>[Cl:27][C:28]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=1[S:35]([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:37])=[O:36]

Participants

4

Reactant 3

HCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 217103385-Bromo-6-ethylpyridin-2-amineHCID 577183134-(N-morpholinylsulfonyl)thiophenol

Product 1

HCID 577181922,4-Dichloro-N-{6-ethyl-5-[4-(morpholine-4-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-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 2,4-dichlorophenylsulfonyl chloride according to General Method 11 step 2. 1H NMR (CDCl3): 8.00 (1 H, d, J 10 Hz, A-ring CH ortho to SO2NH), 7.50 & 6.98 (2×2 H, 2×d, C-ring CH's), 7.45 (1 H, d, J 10 Hz, A-ring CH ortho to Cl), 7.35 (1 H, s, A ring CH ortho to 2×Cl), 7.26 & 6.74 (2×1 H, 2×d, 2×J 10 Hz, pyridyl CH's), 3.63-3.56 (4H, m, CH2CH2), 2.88-2.79 (4H, m, CH2NCH2), 2.72 (3H, q, J 8 Hz, CH2CH3), 1.09 (3 H, t, J 8 Hz, CH2CH3). Hplc (Luna 2, Gradient 5): rt=6.19 minutes. LC/MS rt=6.86 minutes, 588/590 (MH+).

Workup

  1. customrt=6.19 minutes
  2. customLC/MS rt=6.86 minutes, 588/590 (MH+)

Sources & evidence

ORD record
ord-9825e792c0214ccfbcf3c9c2d17e36cc
Source dataset
uspto-grants-2011_02
Patent number
US07893077B2

Reaction notes

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