4-Chloro-2-(2,4-difluoro-benzenesulfonylamino)-benzoic acid → (+/-)-4-Chloro-N-[2-(3,4-dichloro-Phenyl)-propyl]-2-(2,4-difluorobenzenesulfonylamino)-benzamide

HRID 2265187Notes

Reaction equation

HRID 2265187 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])(=[O:14])=[O:13])[CH:3]=1.Cl.[Cl:24][C:25]1[CH:26]=[C:27]([CH:32]([CH3:35])[CH2:33][NH2:34])[CH:28]=[CH:29][C:30]=1[Cl:31]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:34][CH2:33][CH:32]([C:27]2[CH:28]=[CH:29][C:30]([Cl:31])=[C:25]([Cl:24])[CH:26]=2)[CH3:35])=[O:8])=[C:4]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])(=[O:14])=[O:13])[CH:3]=1

Participants

3

Reactant 2

HCID 454647334-Chloro-2-(2,4-difluoro-benzenesulfonylamino)-benzoic acidHCID 687713402-(3,4-Dichlorophenyl)propan-1-amine hydrochloride

Product 1

HCID 11663774(+/-)-4-Chloro-N-[2-(3,4-dichloro-Phenyl)-propyl]-2-(2,4-difluorobenzenesulfonylamino)-benzamide

Procedure

4-Chloro-2-(2,4-difluoro-benzenesulfonylamino)-benzoic acid was coupled with (±)-2-(3,4-dichloro-phenyl)-propylamine hydrochloride as in EXAMPLE 1, Part C. HPLC: RT=12.04 min. MS (ESI−): mass calcd. for C22H17Cl3FN2O3S2, 532.00; m/z found, 531/533 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.41 (s, 1H), 8.00 (ddd, J=8.6, 8.6, 6.0, 1H), 7.61 (d, J=2.0, 1H), 7.42 (d, J=8.2, 1H), 7.32 (d, J=2.1, 1H), 7.11 (d, J=8.4, 1H), 7.08 (dd, J=8.2, 2.1, 1H), 7.03-6.97 (m, 1H), 6.97 (dd, J=8.4, 2.0, 1H), 6.92-6.86 (m, 1H), 6.02-5.95 (br m, 1H), 3.76-3.68 (m, 1H), 3.41-3.31 (m, 1H), 3.11-3.01 (m, 1H), 1.32 (d, J=7.0, 3H).

Sources & evidence

ORD record
ord-d62fd223c5064dbda03dbe21bd6b4a31
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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