2-(3,4-Dichloro-phenyl)-propylamine → N-[2-(3,4-Dichloro-phenyl)-propyl]-2-(2,6-difluoro-benzenesulfonylamino)-4-iodo-benzamide

HRID 1593855Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[S:9]([NH:12][C:13]1[CH:21]=[C:20]([I:22])[CH:19]=[CH:18][C:14]=1[C:15](O)=[O:16])(=[O:11])=[O:10].[Cl:23][C:24]1[CH:25]=[C:26]([CH:31]([CH3:34])[CH2:32][NH2:33])[CH:27]=[CH:28][C:29]=1[Cl:30]>>[Cl:23][C:24]1[CH:25]=[C:26]([CH:31]([CH3:34])[CH2:32][NH:33][C:15](=[O:16])[C:14]2[CH:18]=[CH:19][C:20]([I:22])=[CH:21][C:13]=2[NH:12][S:9]([C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=2[F:8])(=[O:11])=[O:10])[CH:27]=[CH:28][C:29]=1[Cl:30]

Participants

Reactant 2

HCID 658100362-(3,4-Dichloro-phenyl)-propylamine

HCID 687736512-[[(2,6-difluorophenyl)sulfonyl]amino]-4-iodoBenzoic acid

Product 1

HCID 11592589N-[2-(3,4-Dichloro-phenyl)-propyl]-2-(2,6-difluoro-benzenesulfonylamino)-4-iodo-benzamide

Procedure

This compound was prepared from 2-(2,6-difluorobenzenesulfonylamino)-4-iodo-benzoic acid and 2-(3,4-dichloro-phenyl)-propylamine as in EXAMPLE 1, Part C. HPLC: RT=11.98 min. MS (ESI−): mass calcd. for C22H17Cl2F2IN2O3S, 625.3; m/z found, 624 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.63 (s, 1H), 8.02 (d, J=1.5, 1H), 7.54-7.45 (m, 1H), 7.39 (d, J=8.2, 1H), 7.34 (d, J=1.6, 1H), 7.32 (d, J=1.8, 1H), 7.09 (dd, J=8.3, 2.1, 1H), 7.02-6.94 (m, 3H), 6.34-6.32 (br m, 1H), 3.743.65 (m, 1H), 3.40 (ddd, J=13.7, 8.5, 5.6, 1H), 3.14-3.04 (m, 1H), 1.30 (d, J=7.0, 3H).

Sources & evidence

ORD record: ord-c844c270025146b994618d8615d427f7
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07297816B2

Reaction notes

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