(S)-5-(Hydroxymethyl)-2-pyrrolidinone → (S)-1-{4-[4-(3,5-dicyclopropylpyridin-2-yl)piperazine-1-carbonyl]-3-fluorophenyl}-5-hydroxymethylpyrrolidin-2-one

HRID 2411667Notes

Reaction equation

HRID 2411667 reaction equation
[OH:1][CH2:2][C@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.[CH:9]1([C:12]2[C:13]([N:21]3[CH2:26][CH2:25][N:24]([C:27]([C:29]4[CH:34]=[CH:33][C:32](I)=[CH:31][C:30]=4[F:36])=[O:28])[CH2:23][CH2:22]3)=[N:14][CH:15]=[C:16]([CH:18]3[CH2:20][CH2:19]3)[CH:17]=2)[CH2:11][CH2:10]1>>[CH:9]1([C:12]2[C:13]([N:21]3[CH2:22][CH2:23][N:24]([C:27]([C:29]4[CH:34]=[CH:33][C:32]([N:7]5[C@H:3]([CH2:2][OH:1])[CH2:4][CH2:5][C:6]5=[O:8])=[CH:31][C:30]=4[F:36])=[O:28])[CH2:25][CH2:26]3)=[N:14][CH:15]=[C:16]([CH:18]3[CH2:20][CH2:19]3)[CH:17]=2)[CH2:10][CH2:11]1

Participants

3

Reactant 2

HCID 643511(S)-5-(Hydroxymethyl)-2-pyrrolidinoneHCID 71251940HCID 71251940, compound

Product 1

HCID 71252866(S)-1-{4-[4-(3,5-dicyclopropylpyridin-2-yl)piperazine-1-carbonyl]-3-fluorophenyl}-5-hydroxymethylpyrrolidin-2-oneYield 40.6%

Procedure

Using (S)-5-hydroxymethylpyrrolidin-2-one (94 mg) and [4-(3,5-dicyclopropylpyridin-2-yl)piperazin-1-yl](2-fluoro-4-iodophenyl)methanone (400 mg) described in Preparation Example 164 and by the reaction and treatment in the same manner as in Example 1, the title compound (158 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 164 and by the reaction and treatment in the same manner as in Example 1

Sources & evidence

ORD record
ord-ff1abea1a40e4f1f8288359dd6d42fbb
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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