Benzenesulfonyl chloride, 2,4-dichloro- → n-{6-Butyryl-5-[4-(pyrrolidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-2,4-dichloro-benzenesulfonamide

HRID 1366845Notes

Reaction equation

HRID 1366845 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([C:9]([O:11]CCCCC)=O)[N:3]=1.[N:17]1([S:22]([C:25]2[CH:30]=[CH:29][C:28]([SH:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18]1.[Cl:32][C:33]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=1[S:40](Cl)(=[O:42])=[O:41].[CH2:44]([Mg]Cl)[CH2:45][CH3:46]>>[C:9]([C:4]1[N:3]=[C:2]([NH:1][S:40]([C:34]2[CH:35]=[CH:36][C:37]([Cl:39])=[CH:38][C:33]=2[Cl:32])(=[O:42])=[O:41])[CH:7]=[CH:6][C:5]=1[S:31][C:28]1[CH:29]=[CH:30][C:25]([S:22]([N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)(=[O:24])=[O:23])=[CH:26][CH:27]=1)(=[O:11])[CH2:44][CH2:45][CH3:46]

Participants

5

Reactant 4

HCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 577182764-(N-pyrollidylsulfonyl)thiophenolHCID 577182862-Amino-5-iodo-6-pentoxycarbonylpyridineHCID 178455855HCID 178455855, compound

Product 1

HCID 57718228n-{6-Butyryl-5-[4-(pyrrolidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-2,4-dichloro-benzenesulfonamide

Procedure

Prepared from 2-amino-5-iodo-6-pentoxycarbonylpyridine and 4-(N -pyrollidylsulfonyl)thiophenol according to General Method 11 step 1 followed by reaction with 2,4-dichlorophenylsulfonyl chloride according to General Method 11 step 2 and then General Method 11 step 3 employing propyl magnesium chloride. 1H NMR (CDCl3): 8.00 (1 H, d, J 11 Hz, A-ring CH ortho to SO2NH), 7.76 & 7.52 (2×2 H, 2×d, 2×J 10 Hz, Ar CH's of C-ring), 7.61 (1 H, br s, NH), 7.46 (1 H, s, A-ring CH ortho to 2×Cl) 7.32 (1 H, d, J 11 Hz, A-ring CH ortho to Cl), 7.07 & 7.03 (2×1 H, 2×d, 2×J 11 Hz, B-ring CH's), 3.24-3.15 (4H, m, CH2NCH2), 2.89 (2 H, t, J 8 Hz, COCH2), 1.78-1.69 (4 H, m, CH2CH2CH2CH2), 1.63 (2 H, sextet, J 8 Hz, CH2CH3), 0.92 (3 H, t, J 9 Hz, CH3). Hplc (Luna 2, Gradient 5): rt=6.86 minutes. LC/MS rt=7.55 minutes, 614/616 (MH+).

Workup

  1. customrt=6.86 minutes
  2. customLC/MS rt=7.55 minutes, 614/616 (MH+)

Sources & evidence

ORD record
ord-e0e7c67a44774be0a0d3360fc7a2586e
Source dataset
uspto-grants-2011_02
Patent number
US07893077B2

Reaction notes

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