4-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid → (+/-)-4-Chloro-N-[2-(3,4-dichloro-phenyl)-propyl]-2-(quinoxaline-5-sulfonylamino)-benzamide

HRID 2265244Notes

Reaction equation

HRID 2265244 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[C:16]3[N:17]=[CH:18][CH:19]=[N:20][C:21]=3[CH:22]=[CH:23][CH:24]=2)(=[O:14])=[O:13])[CH:3]=1.Cl.[Cl:26][C:27]1[CH:28]=[C:29]([CH:34]([CH3:37])[CH2:35][NH2:36])[CH:30]=[CH:31][C:32]=1[Cl:33]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:36][CH2:35][CH:34]([C:29]2[CH:30]=[CH:31][C:32]([Cl:33])=[C:27]([Cl:26])[CH:28]=2)[CH3:37])=[O:8])=[C:4]([NH:11][S:12]([C:15]2[C:16]3[N:17]=[CH:18][CH:19]=[N:20][C:21]=3[CH:22]=[CH:23][CH:24]=2)(=[O:13])=[O:14])[CH:3]=1

Participants

3

Reactant 2

HCID 160907784-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acidHCID 687713402-(3,4-Dichlorophenyl)propan-1-amine hydrochloride

Product 1

HCID 11628164(+/-)-4-Chloro-N-[2-(3,4-dichloro-phenyl)-propyl]-2-(quinoxaline-5-sulfonylamino)-benzamide

Procedure

The title compound was prepared from 4-chloro-2-(quinoxaline-5-sulfonylamino)-benzoic acid and (±)-2-(3,4-dichloro-phenyl)-propylamine hydrochloride as in EXAMPLE 1, Part C. HPLC: RT=10.78 min. MS (ESI+): mass calcd. for C24H19Cl3N4O3S, 548.02; m/z found, 551/553 [M+H]+, m/z found, 571/575 [M+Na]+. 1H NMR (400 MHz, CDCl3): 11.21 (s, 1H), 9.04 (d, J=1.7, 1H), 8.96 (d, J=1.7, 1H), 8.57 (dd, J=7.3, 1.3, 1H), 8.33 (dd, J=8.5, 1.2, 1H), 7.91-7.87 (m, 1H), 7.71 (d, J=1.9, 1H), 7.39 (d, J=8.2, 1H), 7.29 (d, J=2.0, 1H), 7.04 (dd, J=8.2, 2.0, 1H), 6.99 (d, J=8.4, 1H), 6.88 (dd, J=8.4, 2.0, 1H), 5.82 (s, 1H), 3.70-3.63 (m, 1H), 3.33-3.26 (m, 1H), 3.02-2.98 (m, 1H), 1.30 (d, J=7.0, 3H).

Sources & evidence

ORD record
ord-e7d763946af54989a8c18f4cb476754e
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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