Sodium hydride → 1-(6-Amino-pyridin-2-ylmethyl)-3-(5,6-dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-one

HRID 227116Notes

Reaction equation

HRID 227116 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)=[O:10])[CH:5]=[N:6][C:7]=1[CH3:8].[H-].[Na+].Br[CH2:25][C:26]1[N:31]=[C:30]([NH:32]C(=O)C(F)(F)F)[CH:29]=[CH:28][CH:27]=1>CN(C)C=O>[NH2:32][C:30]1[N:31]=[C:26]([CH2:25][N:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20](=[O:21])[C:11]([C:9]([C:4]3[CH:5]=[N:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=3)=[O:10])=[CH:12]2)[CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 577545393-(5,6-Dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-oneHCID 57754672N-(6-bromomethyl-pyridin-2-yl)-2,2,2-trifluoro-acetamide

Product 1

HCID 577546361-(6-Amino-pyridin-2-ylmethyl)-3-(5,6-dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1, from 75 mg (0.27 mmol) of 3-(5,6-dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-one, 13 mg (0.32 mmol) of 60% sodium hydride, 92 mg (0.32 mmol) of N-(6-bromomethyl-pyridin-2-yl)-2,2,2-trifluoro-acetamide and 0.7 mL of N,N-dimethylformamide. Yield: 20 mg of a white solid: LC-MSD, m/z for C23H20N4O2 [M+H]+=385.1; HPLC retention time: 0.3 min.

Sources & evidence

ORD record
ord-53b00942d9f94e6fac80e70110aae9a0
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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