Methyl p-toluenesulfonate → (S)-1-{4-[4-(3,5-dicyclopropylpyridin-2-yl)piperazine-1-carbonyl]-3-fluorophenyl}-5-methoxymethylpyrrolidin-2-one

HRID 2411668Notes

Reaction equation

HRID 2411668 reaction equation
[CH:1]1([C:4]2[C:5]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([C:21]4[CH:26]=[CH:25][C:24]([N:27]5[C@H:31]([CH2:32][OH:33])[CH2:30][CH2:29][C:28]5=[O:34])=[CH:23][C:22]=4[F:35])=[O:20])[CH2:15][CH2:14]3)=[N:6][CH:7]=[C:8]([CH:10]3[CH2:12][CH2:11]3)[CH:9]=2)[CH2:3][CH2:2]1.S(C1C=CC(C)=CC=1)(O[CH3:40])(=O)=O>>[CH:1]1([C:4]2[C:5]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([C:21]4[CH:26]=[CH:25][C:24]([N:27]5[C@H:31]([CH2:32][O:33][CH3:40])[CH2:30][CH2:29][C:28]5=[O:34])=[CH:23][C:22]=4[F:35])=[O:20])[CH2:15][CH2:14]3)=[N:6][CH:7]=[C:8]([CH:10]3[CH2:12][CH2:11]3)[CH:9]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 71252866(S)-1-{4-[4-(3,5-dicyclopropylpyridin-2-yl)piperazine-1-carbonyl]-3-fluorophenyl}-5-hydroxymethylpyrrolidin-2-one

Product 1

HCID 71252058(S)-1-{4-[4-(3,5-dicyclopropylpyridin-2-yl)piperazine-1-carbonyl]-3-fluorophenyl}-5-methoxymethylpyrrolidin-2-one

Procedure

Using (S)-1-{4-[4-(3,5-dicyclopropylpyridin-2-yl)piperazine-1-carbonyl]-3-fluorophenyl}-5-hydroxymethylpyrrolidin-2-one (130 mg) described in Example 294 and methyl tosylate (41 μL) and by the reaction and treatment in the same manner as in Example 36, the title compound (8 mg) was obtained.

Sources & evidence

ORD record
ord-a1a22ef4ba274a5894320aa3a8d7bea8
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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