2,4-Dichloro-5-methylbenzene-1-sulphonyl chloride → HCID 57718252, compound

HRID 1984586Notes

Reaction equation

HRID 1984586 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5](Br)=[CH:4][N:3]=1.[N:10]1([S:16]([C:19]2[CH:24]=[CH:23][C:22]([SH:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[Cl:26][C:27]1[CH:32]=[C:31]([Cl:33])[C:30]([CH3:34])=[CH:29][C:28]=1[S:35](Cl)(=[O:37])=[O:36]>>[Cl:26][C:27]1[CH:32]=[C:31]([Cl:33])[C:30]([CH3:34])=[CH:29][C:28]=1[S:35]([NH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:25][C:22]2[CH:21]=[CH:20][C:19]([S:16]([N:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)(=[O:18])=[O:17])=[CH:24][CH:23]=2)=[CH:4][N:3]=1)(=[O:37])=[O:36]

Participants

4

Reactant 3

HCID 1199142,4-Dichloro-5-methylbenzene-1-sulphonyl chlorideHCID 8176952-Amino-5-bromo-4-methylpyridineHCID 577182904-(N-piperidinylsulfonyl)thiophenol

Product 1

HCID 57718252HCID 57718252, compound

Procedure

2,4-Dichloro-5-methyl-N-{4-methyl-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamide was prepared from 2-amino-5-bromo-4-methylpyridine and 4-(N-piperidinylsulfonyl)thiophenol according to General Method 11 step 1 followed by reaction with 2,4-dichloro-5-methylphenylsulfonyl chloride according to General Method 11 step 2. 1H NMR (CDCl3): 13.20 (1H, br s, NH), 8.40 (1H, s, A-ring CH ortho to 2×Cl), 8.03 (1H, s, A-ring CH ortho to SO2NH), 7.53 & 7.04 (2×2H, 2×d, 2×J 10 Hz, Ar CH's of C-ring), 7.41 & 7.15 (2×1H, 2×s, pyridyl CH's), 2.91-2.83 (4H, m, CH2NCH2), 2.38 & 2.23 (2×3H, 2×s, 2×CH3), 1.61-1.48 (4H, m, CH2CH2CH2CH2CH2), 1.39-1.28 (2H, m, CH2CH2CH2CH2CH2). Hplc (Luna 2, Gradient 5): rt=6.73 minutes. LC/MS rt=7.43 minutes, 586/588 (MH+).

Workup

  1. customrt=6.73 minutes
  2. customLC/MS rt=7.43 minutes, 586/588 (MH+)

Sources & evidence

ORD record
ord-2e527db7c0404e8597f13ac255fcec4e
Source dataset
uspto-grants-2009_06
Patent number
US07544702B2

Reaction notes

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