Methanesulfonamide → US10023592, Example 158

HRID 518376Notes

Reaction equation

HRID 518376 reaction equation
BrC1C2C(=CC(F)=CC=2)C(=O)NC=1.CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1.FC1C=C2C(C(B3OC(C)(C)C(C)(C)O3)=CN(C)C2=O)=CC=1.ClC1C(OCC2CC2)=CN=C(S(C)(=O)=O)N=1.[CH:70]1([CH2:73][O:74][C:75]2[C:76]([C:85]3[C:94]4[C:89](=[CH:90][C:91]([F:95])=[CH:92][CH:93]=4)[C:88](=[O:96])[N:87]([CH3:97])[CH:86]=3)=[N:77][C:78](S(C)(=O)=O)=[N:79][CH:80]=2)[CH2:72][CH2:71]1.[CH3:98][S:99]([NH2:102])(=[O:101])=[O:100]>>[CH:70]1([CH2:73][O:74][C:75]2[C:76]([C:85]3[C:94]4[C:89](=[CH:90][C:91]([F:95])=[CH:92][CH:93]=4)[C:88](=[O:96])[N:87]([CH3:97])[CH:86]=3)=[N:77][C:78]([NH:102][S:99]([CH3:98])(=[O:101])=[O:100])=[N:79][CH:80]=2)[CH2:71][CH2:72]1

Participants

7

Reactant 6

HCID 72879MethanesulfonamideHCID 2733548Bis(pinacolato)diboraneHCID 847030324-Bromo-7-fluoro-1,2-dihydroisoquinolin-1-oneHCID 1180218984-[5-(Cyclopropylmethoxy)-2-methylsulfonylpyrimidin-4-yl]-7-fluoro-2-methylisoquinolin-1-oneHCID 1180224454-Chloro-5-(cyclopropylmethoxy)-2-methylsulfonylpyrimidineHCID 1238018347-Fluoro-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1-one

Product 1

HCID 118022595US10023592, Example 158

Procedure

The title compound of Example 58, step 2 was treated with 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane in a manner similar to Example 89, step 1 and the resulting 7-fluoro-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1-one was coupled to the title compound of Example 152, step 4 in a manner similar to Example 152, step 5 and the resulting 4-[5-(cyclopropylmethoxy)-2-methylsulfonylpyrimidin-4-yl]-7-fluoro-2-methylisoquinolin-1-one 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 11.15 (s, 1H), 8.55 (s, 1H), 8.36 (dd, J1=9.2 Hz, J2=6.0 Hz, 1H), 8.00 (s, 1H), 7.60 (dd, J1=11.2 Hz, J2=2.4 Hz, 1H), 7.44-7.37 (m, 1H), 3.95 (d, J=7.2 Hz, 2H), 3.58 (s, 3H), 3.32 (s, 3H), 1.15-1.03 (m, 1H), 0.49-0.42 (m, 2H), 0.26-0.20 (m, 2H). LCMS: 419.0 (M+1)+

Sources & evidence

ORD record
ord-d132433bbdfa4b89ad54f7017246ff73
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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