Benzenesulfonyl chloride, 2,4-dichloro- → 6-(2,4-Dichloro-benzenesulfonylamino)-3-[4-(morpholine-4-sulfonyl)-phenylsulfanyl]-pyridine-2-carboxylic acid methyl ester

HRID 1984595Notes

Reaction equation

HRID 1984595 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[C:4]([C:9]([O:11][CH3:12])=[O:10])[N:3]=1.[N:13]1([S:19]([C:22]2[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[Cl:29][C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=1[S:37](Cl)(=[O:39])=[O:38]>>[CH3:12][O:11][C:9]([C:4]1[C:5]([S:28][C:25]2[CH:24]=[CH:23][C:22]([S:19]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)(=[O:21])=[O:20])=[CH:27][CH:26]=2)=[CH:6][CH:7]=[C:2]([NH:1][S:37]([C:31]2[CH:32]=[CH:33][C:34]([Cl:36])=[CH:35][C:30]=2[Cl:29])(=[O:39])=[O:38])[N:3]=1)=[O:10]

Participants

4

Reactant 3

HCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 10657127Methyl 6-amino-3-bromopyridine-2-carboxylateHCID 577183134-(N-morpholinylsulfonyl)thiophenol

Product 1

HCID 577182996-(2,4-Dichloro-benzenesulfonylamino)-3-[4-(morpholine-4-sulfonyl)-phenylsulfanyl]-pyridine-2-carboxylic acid methyl ester

Procedure

Prepared from 2-amino-5-bromo-6-methoxycarbonylpyridine 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): 8.04 (1H, d, J 11 Hz, A-ring CH ortho to SO2NH), 7.62 & 7.42 (2×2 H, 2×d, 2×J 10 Hz, C-ring CH's), 7.43 (1H, s, A-ring CH ortho to 2×Cl), 7.31 (1H, d, J 11 Hz, A ring CH ortho to Cl), 7.28 & 7.18(2×1H, 2×d, 2×J 10 Hz, pyridyl CH's), 3.89 (3H, s, CH3) 3.72-3.63 (4H, m, CH2OCH2), 2.98-2.88 (4H, m, CH2NCH2). Hplc (Luna 2, Gradient 5): rt=6.00 minutes. LC/MS rt=6.69 minutes, 618/620 (MH+).

Workup

  1. customrt=6.00 minutes
  2. customLC/MS rt=6.69 minutes, 618/620 (MH+)

Sources & evidence

ORD record
ord-19cd29482fc04dc492f1ccc98c32c39f
Source dataset
uspto-grants-2009_06
Patent number
US07544702B2

Reaction notes

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