2-Pyridinamine, 5-bromo-6-methyl- → 2,4-Dichloro-N-{6-methyl-5-[4-(morpholine-4-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamide

HRID 1366844Notes

Reaction equation

HRID 1366844 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[C:4]([CH3:9])[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][O:13][CH2:12][CH2:11]1.[Cl:26][C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[S:34](Cl)(=[O:36])=[O:35]>>[Cl:26][C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[S:34]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:25][C:22]2[CH:21]=[CH:20][C:19]([S:16]([N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)(=[O:18])=[O:17])=[CH:24][CH:23]=2)=[C:4]([CH3:9])[N:3]=1)(=[O:36])=[O:35]

Participants

4

Reactant 3

HCID 1706782-Pyridinamine, 5-bromo-6-methyl-HCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 577183134-(N-morpholinylsulfonyl)thiophenol

Product 1

HCID 577181872,4-Dichloro-N-{6-methyl-5-[4-(morpholine-4-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamide

Procedure

Prepared from 2-amino-5-bromo-6-methylpyridine 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): 8.09 (1 H, d, J 10 Hz, A-ring CH ortho to SO2NH), 7.68, 7.35 & 7.12 (3×1 H, 3×d, 3×J 10 Hz, pyridyl CH's & A-ring CH ortho to Cl), 7.58 & 7.08 (2×2 H, 2×d, 2×J 10 Hz, C-ring CH's), 7.46 (1 H, s, A ring CH ortho to 2×Cl), 3.71-3.62 (4H, m, CH2OCH2), 2.94-2.85 (4H, m, CH2NCH2), 2.49 (3H, s, CH1). Hplc (Luna 2, Gradient 5): rt=5.81 minutes. LC/MS rt=6.58 minutes, 574/576 (MH+).

Workup

  1. customrt=5.81 minutes
  2. customLC/MS rt=6.58 minutes, 574/576 (MH+)

Sources & evidence

ORD record
ord-7fb7c3030cb5464783379eae4edbd51e
Source dataset
uspto-grants-2011_02
Patent number
US07893077B2

Reaction notes

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