Sodium hydride → US10023592, Example 248

HRID 575725Notes

Reaction equation

HRID 575725 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[H-].[Na+].[CH:8]1([CH2:11][N:12]2[CH:17]=[C:16]([C:18]3[C:23]([O:24][C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=4[F:32])=[CH:22][N:21]=[C:20](S(C)(=O)=O)[N:19]=3)[CH:15]=[C:14]([CH3:37])[C:13]2=[O:38])[CH2:10][CH2:9]1>CN(C=O)C>[CH:8]1([CH2:11][N:12]2[C:13](=[O:38])[C:14]([CH3:37])=[CH:15][C:16]([C:18]3[C:23]([O:24][C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=4[F:32])=[CH:22][N:21]=[C:20]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[N:19]=3)=[CH:17]2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 72879MethanesulfonamideHCID 1180220591-(Cyclopropylmethyl)-5-[5-(2,4-difluorophenoxy)-2-methylsulfonylpyrimidin-4-yl]-3-methylpyridin-2-one

Product 1

HCID 118021702US10023592, Example 248Yield 54.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methanesulfonamide (68 mg, 0.71 mmol), NaH (28 mg, 0.7 mmol, 60% in mineral oil) and the title compound from step 3 (80 mg, 0.18 mmol) in DMF (2 mL) were reacted in a similar manner as Example 152, step 6 to give the title compound (45.00 mg, yield: 54.4%) as an off-white solid. 1H NMR (CDCl3, 400 MHz) δ 8.81 (s, 1H), 8.60 (d, J=2.0 Hz, 1H), 8.14 (s, 1H), 8.12 (s, 1H), 7.05-6.98 (m, 2H), 6.91-6.89 (m, 1H), 3.87 (d, J=7.2 Hz, 2H), 3.45 (s, 3H), 2.23 (s, 3H), 1.25-1.22 (m, 1H), 0.64-0.59 (m, 2H), 0.40-0.37 (m, 2H). LCMS: 463.1 (M+H)+

Sources & evidence

ORD record
ord-c4c636c457034bda88f61c12d2ec8d82
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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