Dimethylformamide → US10023592, Example 242

HRID 575716Notes

Reaction equation

HRID 575716 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:7]=2[C:16]2[CH:17]=[C:18]([CH3:23])[C:19](=O)[NH:20][CH:21]=2)[CH2:3][CH2:2]1.[C:24]([O-:27])([O-])=O.[K+].[K+].[CH3:30][C:31](=O)OCC.[CH3:36]N(C=O)C>>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:13])=[O:14])=[CH:8][C:7]=2[C:16]2[CH:17]=[C:30]([CH3:31])[C:24](=[O:27])[N:20]([CH2:19][CH:18]3[CH2:36][CH2:23]3)[CH:21]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1180216505-[2-(cyclopropylmethoxy)-5-methylsulfonylphenyl]-3-methyl-1H-pyridin-2-one

Product 1

HCID 118022485US10023592, Example 242

Procedure

The title compound of step 1 (80 mg), K2CO3 (77 mg, 0.56 mmol) bromomethylcyclopropane (62 mg, 0.46 mmol) in DMF (2 mL) were heated at 70° C. for 4 h. EA extractive work up and preparative HPLC gave the title compound (17 mg) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 7.85-7.83 (m, 2H), 7.67 (d, J=2.0 Hz, 1H), 7.53 (s, 1H), 7.03 (d, J=9.2 Hz, 1H), 3.95 (d, J=6.8 Hz, 1H), 3.89 (d, J=7.2 Hz, 1H), 3.07 (s, 3H), 2.23 (s, 3H), 1.34-1.26 (m, 2H), 0.68-0.65 (m, 2H), 0.65-0.61 (m, 2H), 0.44-0.43 (m, 2H), 0.38-0.37 (m, 2H). LCMS: 388.2 (M+1)+

Sources & evidence

ORD record
ord-523ed8eab942428492d3d23ea4246701
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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