N-(2-Iodophenyl)-N'-methylurea → N-(2-{[6-(4-Fluorophenyl)-2-naphthyl]sulfonyl}phenyl)-N'-methylurea

HRID 735345Notes

Reaction equation

HRID 735345 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][CH3:12])=[O:10].[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[CH:26]=[C:25]([S:30]([O-:32])=[O:31])[CH:24]=[CH:23]3)=[CH:16][CH:15]=1.[Na+]>>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[CH:26]=[C:25]([S:30]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:8][C:9]([NH:11][CH3:12])=[O:10])(=[O:32])=[O:31])[CH:24]=[CH:23]3)=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 47027879N-(2-Iodophenyl)-N'-methylureaHCID 68900681Sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate

Product 1

HCID 68901810N-(2-{[6-(4-Fluorophenyl)-2-naphthyl]sulfonyl}phenyl)-N'-methylurea

Procedure

Prepared according to the method of Example 6 Step 4 using N-(2-iodophenyl)-N′-methylurea and sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate, to give the title compound as a white solid (81 mg). 1H NMR (500 MHz, d6-DMSO): δ 8.81 (1H, s), 8.34 (2H, s), 8.18 (2H, dd, J=8.6, 21.9 Hz), 8.08-8.02 (2H, m), 7.97 (1H, d, J=8.3 Hz), 7.90 (2H, dd, J=5.5, 8.7 Hz), 7.84 (1H, dd, J=1.7, 8.6 Hz), 7.61-7.57 (1H, m), 7.52 (1H, s), 7.37 (2H, t, J=8.8 Hz), 7.25 (1H, t, J=7.6 Hz), 2.56 (3H, d, J=4.4 Hz); m/z (ES+) 411 [MH+].

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-eb1a7b91722c4eac8d2cc71a32c243fe
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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