Ethanesulfonamide → US10023592, Example 249

HRID 518456Notes

Reaction equation

HRID 518456 reaction equation
[CH:1]1([CH2:4][N:5]2[CH:10]=[C:9]([C:11]3[C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=4[F:25])=[CH:15][N:14]=[C:13](S(C)(=O)=O)[N:12]=3)[CH:8]=[C:7]([CH3:30])[C:6]2=[O:31])[CH2:3][CH2:2]1.[CH2:32]([S:34]([NH2:37])(=[O:36])=[O:35])[CH3:33]>>[CH:1]1([CH2:4][N:5]2[C:6](=[O:31])[C:7]([CH3:30])=[CH:8][C:9]([C:11]3[C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=4[F:25])=[CH:15][N:14]=[C:13]([NH:37][S:34]([CH2:32][CH3:33])(=[O:36])=[O:35])[N:12]=3)=[CH:10]2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 73702EthanesulfonamideHCID 1180220591-(Cyclopropylmethyl)-5-[5-(2,4-difluorophenoxy)-2-methylsulfonylpyrimidin-4-yl]-3-methylpyridin-2-one

Product 1

HCID 118021861US10023592, Example 249

Procedure

The title compound of Example 248, step 3 was treated with EtSO2NH2 instead of MeSO2NH2 in a manner similar to Example 248, step 4 to give the title compound. 1H NMR (CDCl3, 400 MHz) δ 9.09 (s, 1H), 8.60 (s, 1H), 8.16 (s, 1H), 8.11 (s, 1H), 7.04-6.96 (m, 2H), 6.91-6.89 (m, 1H), 3.87 (d, J=7.2 Hz, 2H), 3.64 (q, J=7.2 Hz, 2H), 2.22 (s, 3H), 1.44 (t, J=7.2 Hz, 3H), 1.25-1.23 (m, 1H), 0.62-0.60 (m, 2H), 0.38-0.37 (m, 2H). LCMS: 477.2 (M+H)+

Sources & evidence

ORD record
ord-d0286071d07b4b8aadc3835bc27b8259
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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