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

HRID 1366842Notes

Reaction equation

HRID 1366842 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][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]=[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][O:13][CH2:14][CH2:15]3)(=[O:18])=[O:17])=[CH:24][CH:23]=2)=[CH:4][N:3]=1)(=[O:39])=[O:38]

Participants

4

Reactant 3

HCID 8176952-Amino-5-bromo-4-methylpyridineHCID 27366752-Chloro-4-(trifluoromethyl)benzenesulfonyl chlorideHCID 577183134-(N-morpholinylsulfonyl)thiophenol

Product 1

HCID 669713912-Chloro-N-{4-methyl-5-[4-(morpholine-4-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-4-trifluoromethyl-benzenesulfonamide

Procedure

Prepared from 2-amino-5-bromo-4-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 2. 1H NMR (CDCl3): 13.25 (1 H, br s, N11), 8.39 (1 H, s, A-ring CH ortho to Cl), 8.32 (1 H, d, J 11 Hz, A-ring CH ortho to SO2NH), 7.65 & 7.15 (2×1 H, 2×s, pyridyl CH's), 7.62 (1 H, d, J 11 Hz, A-ring CH ortho to CF3), 7.55 & 7.10 (2×2 H, 2×d, 2×J 10 Hz, Ar CH's of C-ring), 3.70-3.60 (4H, m, CH2OCH2), 2.95-2.84 (4H, m, CH2NCH2), 2.23 (3H, s, CH3). Hplc (Luna 2, Gradient 5): rt=6.01 minutes. LC/MS rt=6.75 minutes, 608 (MH+).

Workup

  1. customrt=6.01 minutes
  2. customLC/MS rt=6.75 minutes, 608 (MH+)

Sources & evidence

ORD record
ord-cba491eb31f74c4b810f47669b2b261a
Source dataset
uspto-grants-2011_02
Patent number
US07893077B2

Reaction notes

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