2-Mesitylenesulfonyl chloride → N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}-2,4,6-trimethylbenzenesulfonamide hydrochloride

HRID 346766Notes

Reaction equation

HRID 346766 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[CH:4][C:3]=1[NH:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24].[C:32]1([CH3:44])[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[C:33]=1[S:40]([Cl:43])(=[O:42])=[O:41]>>[ClH:43].[N:8]1([C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:40]([C:33]3[C:34]([CH3:39])=[CH:35][C:36]([CH3:38])=[CH:37][C:32]=3[CH3:44])(=[O:42])=[O:41])=[C:3]([NH:22][S:23]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)(=[O:25])=[O:24])[CH:4]=2)[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 130462-Mesitylenesulfonyl chlorideHCID 22272501N-(2-amino-5-(4-t-butyloxycarbonyl-1,4-diazepan-1-yl)-phenyl}benzenesulfonamide

Product 1

HCID 10166651N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}-2,4,6-trimethylbenzenesulfonamide hydrochloride

Procedure

The compound was synthesized from of N-{2-amino-5-(4-t-butyloxycarbonyl-1,4-diazepan-1-yl)-phenyl}benzenesulfonamide and 2-mesitylenesulfonylchloride (59 mg, 0.27 mmol) to give 56 mg as purple solid. M+1 529.3 Calcd 529.70; 1HNMR δ 7.80–7.47 (m, 5H), 6.93 (s br, 2H), 6.64 (d, 1H), 6.46–6.39 (m, 2H), 3.60 (app t, 2H), 3.39 (app t, 2H), 3.21 (app t, 2H), 3.12 (app t, 2H), 2.36 (s, 6H), 2.26 (s, 3H), 2.08–2.00 (m, 2H).

Workup

  1. customto give 56 mg as purple solid

Sources & evidence

ORD record
ord-14ddab2081ca4c1a92b560da745c3a5d
Source dataset
uspto-grants-2007_02
Patent number
US07173035B2

Reaction notes

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