Triethylamine → N-[1-(4-{2-[2-Oxo-4-(thiophen-2-ylmethoxy)-2H-pyridin-1-yl]-ethyl}-benzyl)-piperidin-4-yl]-acetamide

HRID 564105Notes

Reaction equation

HRID 564105 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.C(N(CC)CC)C.CS(Cl)(=O)=O.[NH:37]1[CH2:42][CH2:41][CH:40]([NH:43][C:44](=[O:46])[CH3:45])[CH2:39][CH2:38]1>C(Cl)Cl.C(#N)C.O>[O:24]=[C:12]1[CH:13]=[C:14]([O:17][CH2:18][C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[CH:15]=[CH:16][N:11]1[CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:37]2[CH2:42][CH2:41][CH:40]([NH:43][C:44](=[O:46])[CH3:45])[CH2:39][CH2:38]2)=[CH:4][CH:5]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14451564-AcetamidopiperidineHCID 670068591-[2-(4-Hydroxymethyl-phenyl)-ethyl]-4-(thiophen-2-ylmethoxy)-1H-pyridin-2-one

Product 1

HCID 58042709N-[1-(4-{2-[2-Oxo-4-(thiophen-2-ylmethoxy)-2H-pyridin-1-yl]-ethyl}-benzyl)-piperidin-4-yl]-acetamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To 45 mg (0.13 mmol) 1-[2-(4-hydroxymethyl-phenyl)-ethyl]-4-(thiophen-2-ylmethoxy)-1H-pyridin-2-one (example 2.1a) in 3.0 mL DCM is added 55 μL triethylamine (0.40 mmol) and subsequently 20 μL (0.26 mmol) methanesulfonyl chloride at RT. The reaction mixture is stirred 1 h at RT and then 37 mg (0.40 mmol) N-piperidin-4-yl-acetamide is added. The mixture is stirred overnight at RT and is directly added to a reverse HPLC for purification (Zorbax stable bond, C18, 7 μm; water (0.15% formic acid)/acetonitrile 95:5 to 10:90).

Workup

  1. stirringThe mixture is stirred overnight at RT

Sources & evidence

ORD record
ord-3fba35c25b7746479a35eeb228846058
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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