1,3-Propanesultam → US10023592, Example 156

HRID 518374Notes

Reaction equation

HRID 518374 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:7]([C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19](=[O:26])[N:18]([CH3:27])[CH:17]=3)=[N:8][C:9](S(C)(=O)=O)=[N:10][CH:11]=2)[CH2:3][CH2:2]1.[O:28]=[S:29]1(=[O:34])[CH2:33][CH2:32][CH2:31][NH:30]1>>[CH:1]1([CH2:4][O:5][C:6]2[C:7]([C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19](=[O:26])[N:18]([CH3:27])[CH:17]=3)=[N:8][C:9]([N:30]3[CH2:31][CH2:32][CH2:33][S:29]3(=[O:34])=[O:28])=[N:10][CH:11]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 6421571,3-PropanesultamHCID 118021982US10023592, Example 311

Product 1

HCID 118021873US10023592, Example 156

Procedure

The title compound of Example 152, step 5 was treated with 1,1-dioxidoisothiazolidine instead of MeSO2NH2 in a manner similar to Example 152, step 6 to give the title compound. 1H NMR (DMSO-d6, 400 MHz) δ 8.56 (s, 1H), 8.30 (d, J=8.0 Hz, 1H), 7.86 (s, 1H), 7.77 (d, J=8.0 Hz, 1H), 7.67 (t, J=7.6 Hz, 1H), 7.55 (t, J=7.6 Hz, 1H), 3.93-3.91 (m, 4H), 3.59 (s, 3H), 2.38-2.31 (m, 2H), 1.06-1.01 (m, 1H), 0.44-0.39 (m, 2H), 0.20-0.16 (m, 2H). LCMS: 427.1 (M+H)+

Sources & evidence

ORD record
ord-834e06b329bc45c0b18cc6c58ab87cb9
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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