p-Nitrophenylacetonitrile → 4-Chloro-2-(2,6-difluoro-benzenesulfonylamino)-N-[2-(4-nitro-phenyl)-propyl]-benzamide

HRID 2265220Notes

Reaction equation

HRID 2265220 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([NH:11][S:12]([C:15]2[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=2[F:22])(=[O:14])=[O:13])[CH:3]=1.Cl.[N+:24]([C:27]1[CH:32]=[CH:31][C:30]([CH:33]([CH3:36])[CH2:34][NH2:35])=[CH:29][CH:28]=1)([O-:26])=[O:25].[N+](C1C=CC(CC#N)=CC=1)([O-])=O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:35][CH2:34][CH:33]([C:30]2[CH:31]=[CH:32][C:27]([N+:24]([O-:26])=[O:25])=[CH:28][CH:29]=2)[CH3:36])=[O:7])=[C:4]([NH:11][S:12]([C:15]2[C:16]([F:22])=[CH:17][CH:18]=[CH:19][C:20]=2[F:21])(=[O:14])=[O:13])[CH:3]=1

Participants

4

Reactant 3

HCID 68386p-NitrophenylacetonitrileHCID 3029819beta-Methyl-p-nitrophenethylamine hydrochlorideHCID 687704442-(2,6-Difluoro-benzenesulfonylamino)-4-chloro-benzoic acid

Product 1

HCID 116991274-Chloro-2-(2,6-difluoro-benzenesulfonylamino)-N-[2-(4-nitro-phenyl)-propyl]-benzamide

Procedure

This compound was prepared from 4-chloro-2-(2,6-difluoro-benzenesulfonylamino)-benzoic acid and 2-(4-nitro-phenyl)-propylamine hydrochloride (prepared as in EXAMPLE 5, substituting 4-nitrophenylacetonitrile in Part A) as in Example 1, Part C. HPLC: RT=10.37 min. MS (ESI−): mass calcd. for C22H18ClF2N3O5S, 509.9; m/z found, 509 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.63 (s, 1H), 8.18 (d, J=8.6, 1H), 7.69 (d, J=1.7, 1H), 7.56-7.46 (m, 1H), 7.42 (d, J=8.6, 2H), 7.15 (d, J=8.5, 1H), 7.02-6.94 (m, 1H), 6.19-6.17 (br m, 1H), 3.79-3.70 (m, 1H), 3.57-3.49 (m, 1H), 3.33-3.23 (m, 1H), 1.38 (d, J=6.9, 3H).

Workup

  1. customprepared as in EXAMPLE 5

Sources & evidence

ORD record
ord-e902e91f09194918aef66e222ad0b0a4
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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