Triethylamine → HCID 58042804, compound

HRID 564138Notes

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[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[CH:13][C:12]2=[O:25])=[CH:5][CH:4]=1.[NH:26]1[CH2:31][CH2:30][CH:29]([NH:32][C:33](=[O:35])[CH3:34])[CH2:28][CH2:27]1.C(N(CC)CC)C.CS(Cl)(=O)=O>>[O:25]=[C:12]1[CH:13]=[C:14]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=2)[CH:15]=[CH:16][N:11]1[CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:26]2[CH2:31][CH2:30][CH:29]([NH:32][C:33](=[O:35])[CH3:34])[CH2:28][CH2:27]2)=[CH:4][CH:5]=1

Participants

Reactant 4

HCID 8471Triethylamine

HCID 31297Methanesulfonyl chloride

HCID 14451564-Acetamidopiperidine

HCID 67006678HCID 67006678, compound

Product 1

HCID 58042804HCID 58042804, compound

Procedure

N-[1-(4-{2-[2-Oxo-4-(pyridin-4-ylmethoxy)-2H-pyridin-1-yl]-ethyl}-benzyl)-piperidin-4-yl]-acetamide is prepared as example 10.1b from 80 mg (0.24 mmol) 1-[2-(4-hydroxymethylphenyl)-ethyl]-4-(pyridin-4-ylmethoxy)-1H-pyridin-2-one (example 10.1a), 101 mg (0.71 mmol) N-piperidin-4-yl-acetamide, 99 μL triethylamine (0.71 mmol) and subsequently 37 μL (0.48 mmol) methanesulfonyl chloride. The product is purified via reverse HPLC chromatography (Zorbax stable bond, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90).

Workup

customThe product is purified via reverse HPLC chromatography (Zorbax stable bond, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90)

Sources & evidence

ORD record: ord-84514e3f263b48179b219a31c8b8aa6c
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067590B2

Reaction notes

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