Benzenesulfonyl chloride → HCID 131726128, compound

HRID 856916Notes

Reaction equation

Cl.F[C:3]1[CH:4]=[C:5]([S:10]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([N:24]3[CH2:30][CH2:29][CH2:28][N:27]([CH3:31])[CH2:26][CH2:25]3)=[CH:16][CH:15]=2)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1F.C1(S([Cl:41])(=O)=O)C=CC=CC=1>>[ClH:41].[CH2:28]([N:27]1[CH2:31][CH2:30][N:24]([C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]([NH:13][S:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:3][CH:4]=3)(=[O:12])=[O:11])=[CH:15][CH:16]=2)[CH2:25][CH2:26]1)[CH3:29]

Participants

Reactant 2

HCID 7369Benzenesulfonyl chloride

HCID 131726127HCID 131726127, compound2×

Product 1

HCID 131726128HCID 131726128, compound

Procedure

The title compound was prepared from (intermediate 3 after reduction according to Method A) 4-(4-ethyl-1-piperazinyl)-1-naphthylamine (0.241 g, 0.945 mmol) and benzenesulfonyl chloride (0.121 mL, 0.945 mmol) by the method described above to yield HCl-salt 0.210 g (51%); 1H NMR (CD3OD) δ 8.19–8.15 (m, 1H), 7.94–7.90 (m, 1H), 7.70–7.66 (m, 2H), 7.56–7.46 (m, 2H), 7.44–7.36 (m, 3H), 7.19 (d, J=8.0 Hz, 1H), 7.11 (d, J=8.0 Hz, 1H), 3.75–3.40 (m, 6H), 3.34 (q, J=7.6 Hz, 2H), 3.25–3.10 (m, 2H), 1.43 (tr, J=7.6 Hz, 3H); MS(posEI) m/z 387 (M+).

Sources & evidence

ORD record: ord-656d31bad6a04817b6baba4c76e97d8a
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144883B2

Reaction notes

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