Methyl iodide → 3-Chloro-pyridine-2-carboxylic acid methyl-[4-methyl-5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide

HRID 1774869Notes

Reaction equation

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

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 24758Sodium hydride

HCID 866792083-Chloro-pyridine-2-carboxylic acid [4-methyl-5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide

Product 1

HCID 866792143-Chloro-pyridine-2-carboxylic acid methyl-[4-methyl-5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide

Procedure

In analogy to the procedure described for the preparation of example 195, 3-chloro-pyridine-2-carboxylic acid [4-methyl-5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide (example 224) has been reacted with sodium hydride and methyl iodide to give the title compound as light brown amorphous solid. MS: 435.5 (M+H+).

Sources & evidence

ORD record: ord-d3b4e73535594ad08a511254374f0440
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260408B2

Reaction notes

Loading…