2-Bromoethyl methyl ether → US10023592, Example 244

HRID 575718Notes

Reaction equation

HRID 575718 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:22])[NH:20][CH:21]=2)[CH2:3][CH2:2]1.Br[CH2:25][CH2:26][O:27][CH3:28].BrCC1CC1>>[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:22])[N:20]([CH2:25][CH2:26][O:27][CH3:28])[CH:21]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 809722-Bromoethyl methyl etherHCID 81503BromomethylcyclopropaneHCID 1180216505-[2-(cyclopropylmethoxy)-5-methylsulfonylphenyl]-3-methyl-1H-pyridin-2-one

Product 1

HCID 118022108US10023592, Example 244

Procedure

The title compound from Example 242, step 1 was reacted in a manner similar to Example 242, step 2 except that 1-bromo-2-methoxyethane was substituted for bromomethylcyclopropane to give the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.86-7.83 (m, 2H), 7.65 (d, J=1.6 Hz, 1H), 7.59 (s, 1H), 7.03 (d, J=8.4 Hz, 1H), 4.22 (t, J=4.8 Hz, 1H), 3.96 (d, J=6.8 Hz, 1H), 3.74 (t, J=4.8 Hz, 1H), 3.34 (s, 3H), 3.07 (s, 3H), 2.23 (s, 3H), 1.30-1.27 (m, 1H), 0.70-0.66 (m, 2H), 0.40-0.36 (m, 2H). LCMS: 392.2 (M+1)+

Sources & evidence

ORD record
ord-8b135fd0e5ee4017b81d6540bd396fd8
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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