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

HRID 1984597Notes

Reaction equation

HRID 1984597 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]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:28]=1[S:37](Cl)(=[O:39])=[O:38]>>[Cl:26][C:27]1[CH:32]=[C:31]([C:33]([F:35])([F:34])[F:36])[CH:30]=[CH:29][C:28]=1[S:37]([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:39])=[O:38]

Participants

4

Reactant 3

HCID 1706782-Pyridinamine, 5-bromo-6-methyl-HCID 27366752-Chloro-4-(trifluoromethyl)benzenesulfonyl chlorideHCID 577183134-(N-morpholinylsulfonyl)thiophenol

Product 1

HCID 577182702-Chloro-N-{6-methyl-5-[4-(morpholine-4-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-4-trifluoromethyl-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-chloro-4-trifluoromethylphenylsulfonyl chloride according to General Method 11 step 1. 1H NMR (CDCl3): 8.24 (1H, d, J 10 Hz, Ar CH ortho to SO2NH), 7.65 (1 H, s, A-ring CH ortho to Cl & CF3), 7.61-7.48 (4H, m, Ar CH's), 7.03 (2H, d, J 9 Hz, Ar CH's), 6.81 (1H, d, J 11 Hz, Ar CH), 3.66-3.58 (4H, m, CH2OCH2), 2.90-2.81 (4H, m, CH2NCH2), 2.41 (3H, s, CH3). Hplc (Luna 2, Gradient 5): rt=5.94 minutes. LC/MS rt=6.60 minutes, 608 (MH+).

Workup

  1. customrt=5.94 minutes
  2. customLC/MS rt=6.60 minutes, 608 (MH+)

Sources & evidence

ORD record
ord-08c16d0e764246e49ece2a834d364467
Source dataset
uspto-grants-2009_06
Patent number
US07544702B2

Reaction notes

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