p-Aminoacetophenone → 1-(4-{[6-(3-Chloropyridin-2-yl)-1,1-dioxido-1,2-benzisothiazol-3-yl]amino}phenyl)ethanone

HRID 1434716Notes

Reaction equation

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

Participants

Reactant 2

HCID 7468p-Aminoacetophenone

HCID 178527199HCID 178527199, compound

Product 1

HCID 115024691-(4-{[6-(3-Chloropyridin-2-yl)-1,1-dioxido-1,2-benzisothiazol-3-yl]amino}phenyl)ethanone

Procedure

The title compound was prepared by reacting the product of Example 1B (0.1574 g, 0.53 mmol) and 4′-aminoacetophenone (0.0876 g, 0.65 mmol) using the procedure as described in Example 1C. MS (ESI+) m/z 412 (M+H)+; (ESI−) m/z 410 (M−H)−; 1H NMR (300 MHz, CD3OD) δ 2.63 (s, 3H), 7.51 (dd, J=8.1, 4.7 Hz, 1H), 8.07 (dd, J=8.1, 1.4 Hz, 1H), 8.11 (s, 4H), 8.19 (dd, J=8.0, 1.5 Hz, 1H), 8.30 (dd, 1H), 8.45 (d, J=8.1 Hz, 1H), 8.65 (dd, J=4.7, 1.4 Hz, 1H).

Sources & evidence

ORD record: ord-cd3e9dfddca94785a20a7fb36fbb6b26
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615570B2

Reaction notes

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