Methanesulfonamide → US10023592, Example 172

HRID 575661Notes

Reaction equation

HRID 575661 reaction equation
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])=[CH:6][N:5]=[C:4](S(C)(=O)=O)[N:3]=1.[CH3:21][N:22]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[C:29]2[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=2[C:23]1=[O:41].[CH3:42][S:43]([NH2:46])(=[O:45])=[O:44]>>[F:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[O:8][C:7]1[C:2]([C:30]2[C:29]3[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=3[C:23](=[O:41])[N:22]([CH3:21])[CH:31]=2)=[N:3][C:4]([NH:46][S:43]([CH3:42])(=[O:45])=[O:44])=[N:5][CH:6]=1

Participants

4

Reactant 3

HCID 72879MethanesulfonamideHCID 1180215444-Chloro-5-(2,4-difluorophenoxy)-2-methylsulfonylpyrimidineHCID 1238019002-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6,7,8-tetrahydroisoquinolin-1-one

Product 1

HCID 118021749US10023592, Example 172

Procedure

The title compound of Example 149, step 3 was reacted with the title compound of Example 163, step 3 in a manner similar to Example 163, step 4 and the resulting product was treated with MeSO2NH2 in a manner similar to Example 163, step 5 to give the title compound. 1H NMR (DMSO-d6, 400 MHz): δ 8.16 (s, 1H), 7.46 (s, 1H), 7.25-7.20 (m, 1H), 6.90-6.84 (m, 2H), 3.34 (s, 3H), 2.80 (s, 3H), 2.41-2.29 (m, 4H), 1.60-1.48 (m, 4H). LCMS: 463.1 (M+H)+

Sources & evidence

ORD record
ord-e8dbd83f12a64c9885694f927f353b22
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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