Pyrrolidine → 1-[2-(4-Pyrrolidin-1-ylmethyl-phenyl)-ethyl]-4-(thiophen-2-ylmethoxy)-1H-pyridin-2-one

HRID 564106Notes

Reaction equation

HRID 564106 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)=[CH:13][C:12]2=[O:24])=[CH:5][CH:4]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>>[N:25]1([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)=[CH:13][C:12]3=[O:24])=[CH:5][CH:4]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 670068591-[2-(4-Hydroxymethyl-phenyl)-ethyl]-4-(thiophen-2-ylmethoxy)-1H-pyridin-2-one

Product 1

HCID 580426901-[2-(4-Pyrrolidin-1-ylmethyl-phenyl)-ethyl]-4-(thiophen-2-ylmethoxy)-1H-pyridin-2-one

Procedure

1-[2-(4-Pyrrolidin-1-ylmethyl-phenyl)-ethyl]-4-(thiophen-2-ylmethoxy)-1H-pyridin-2-one is prepared as example 2.1b from 45 mg (mg (0.13 mmol) 1-[2-(4-hydroxymethyl-phenyl)-ethyl]-4-(thiophen-2-ylmethoxy)-1H-pyridin-2-one (example 2.1a) and 22 μL (0.26 mmol) pyrrolidine. The product is purified via reverse HPLC chromatography (Waters X-Bridge; water (0.15% NH4OH)/acetonitrile 95:5 to 10:90 and then Stable bond, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90).

Workup

  1. customThe product is purified via reverse HPLC chromatography (Waters X-Bridge

Sources & evidence

ORD record
ord-00e971eef8f84c71b5f10e4bb16ccf99
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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