Methanesulfonamide → US10023592, Example 153

HRID 575641Notes

Reaction equation

HRID 575641 reaction equation
Cl[C:2]1[C:7]([O:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[CH:6][N:5]=[C:4](S(C)(=O)=O)[N:3]=1.[CH3:17][N:18]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:21]=[C:20]([CH3:33])[C:19]1=[O:34].[CH3:35][S:36]([NH2:39])(=[O:38])=[O:37]>>[CH:10]1([CH2:9][O:8][C:7]2[C:2]([C:22]3[CH:21]=[C:20]([CH3:33])[C:19](=[O:34])[N:18]([CH3:17])[CH:23]=3)=[N:3][C:4]([NH:39][S:36]([CH3:35])(=[O:38])=[O:37])=[N:5][CH:6]=2)[CH2:11][CH2:12]1

Participants

4

Reactant 3

HCID 72879MethanesulfonamideHCID 712703091,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydropyridin-2-oneHCID 1180224454-Chloro-5-(cyclopropylmethoxy)-2-methylsulfonylpyrimidine

Product 1

HCID 118022186US10023592, Example 153

Procedure

The title compound of Example 152, step 4 was reacted with 1,3-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one in a manner similar to Example 152, step 5 and the resulting product was treated with MeSO2NH2 in a manner similar to Example 152, step 6 to give the title compound. 1H NMR (DMSO-d6, 400 MHz) δ 10.97 (s, 1H), 8.67 (s, 1H), 8.42 (s, 1H), 8.14 (s, 1H), 4.03 (d, J=6.4 Hz, 2H), 3.54 (s, 3H), 3.35 (s, 3H), 2.08 (s, 3H), 1.33-1.31 (m, 1H), 0.63-0.61 (m, 2H), 0.38-0.37 (m, 2H). LCMS: 365.0 (M+1)+

Sources & evidence

ORD record
ord-d1a7f3e89fbd4ad78be1dfadea2dd888
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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