1,3-Propanesultam → US10023592, Example 171

HRID 575660Notes

Reaction equation

HRID 575660 reaction equation
[F:1][C:2]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[C:6]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18](=[O:25])[N:17]([CH3:26])[CH:16]=2)=[N:7][C:8](S(C)(=O)=O)=[N:9][CH:10]=1.[O:32]=[S:33]1(=[O:38])[CH2:37][CH2:36][CH2:35][NH:34]1>>[F:1][C:2]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[C:6]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18](=[O:25])[N:17]([CH3:26])[CH:16]=2)=[N:7][C:8]([N:34]2[CH2:35][CH2:36][CH2:37][S:33]2(=[O:38])=[O:32])=[N:9][CH:10]=1

Participants

3

Reactant 2

HCID 6421571,3-PropanesultamHCID 118021317US10023592, Example 151

Product 1

HCID 118021626US10023592, Example 171

Procedure

The title compound of Example 151 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 8.63 (s, 1H), 8.24 (d, J=8.0 Hz, 1H), 7.86 (s, 1H), 7.83 (d, J=8.0 Hz, 1H), 7.65 (t, J=7.2 Hz, 1H), 7.53 (t, J=7.2 Hz, 1H), 7.31-7.26 (m, 1H), 7.13-7.07 (m, 1H), 6.89-6.87 (m, 1H), 3.97 (t, J=6.4 Hz, 2H), 3.57 (t, J=7.2 Hz, 2H), 3.54 (s, 3H), 2.40-2.33 (m, 2H). LCMS: 485.2 (M+H)+

Sources & evidence

ORD record
ord-c5b35feecf844b7189aa0471d5c67bed
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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