Methanesulfonamide → US10023592, Example 154

HRID 575642Notes

Reaction equation

HRID 575642 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:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:37]3[CH:38]=[N:39][N:40]([CH3:42])[CH:41]=3)[CH:24]=2)[C:19]1=[O:43].[CH3:44][S:45]([NH2:48])(=[O:47])=[O:46]>>[CH:10]1([CH2:9][O:8][C:7]2[C:2]([C:26]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:37]5[CH:38]=[N:39][N:40]([CH3:42])[CH:41]=5)[CH:24]=4)[C:19](=[O:43])[N:18]([CH3:17])[CH:27]=3)=[N:3][C:4]([NH:48][S:45]([CH3:44])(=[O:47])=[O:46])=[N:5][CH:6]=2)[CH2:11][CH2:12]1

Participants

4

Reactant 3

HCID 72879MethanesulfonamideHCID 1180224454-Chloro-5-(cyclopropylmethoxy)-2-methylsulfonylpyrimidineHCID 1237513492-Methyl-6-(1-methylpyrazol-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1-one

Product 1

HCID 118021812US10023592, Example 154

Procedure

The title compound of Example 152, step 4 was reacted with the title compound of Example 46 step 2 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 (CDCl3, 400 MHz) δ 11.15 (s, 1H), 8.56 (s, 1H), 8.27 (s, 1H), 8.25 (d, J=7.6 Hz, 1H), 7.98 (s, 1H), 7.79 (s, 1H), 7.77 (d, J=9.6 Hz, 1H), 7.70 (s, 1H), 3.95 (d, J=7.2 Hz, 2H), 3.85 (s, 3H), 3.57 (s, 3H), 3.32 (s, 3H), 1.00-0.99 (m, 1H), 0.37-0.32 (m, 2H), 0.14-0.12 (m, 2H). LCMS: 481.0 (M+1)+

Sources & evidence

ORD record
ord-bba04d43dcc844599ace4348d04b01ee
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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