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

HRID 227115Notes

Reaction equation

HRID 227115 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([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])=[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.FC(F)(F)C(N)=O>CO.C(NCC)C.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:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[C:7]([CH3:8])[N:6]=3)=[O:10])=[CH:12]2)[CH:27]=[CH:28][CH:29]=1

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 67717TrifluoroacetamideHCID 577545223-(5,6-Dimethyl-pyridine-2-carbonyl)-1H-quinolin-4-oneHCID 57754672N-(6-bromomethyl-pyridin-2-yl)-2,2,2-trifluoro-acetamide

Product 1

HCID 577545491-(6-Amino-pyridin-2-ylmethyl)-3-(5,6-dimethyl-pyridine-2-carbonyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8021DiethylamineSolvent

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1, from 127 mg (0.46 mmol) of 3-(5,6-dimethyl-pyridine-2-carbonyl)-1H-quinolin-4-one, 22 mg (0.55 mmol) of 60% sodium hydride, 155 mg (0.55 mmol) of N-(6-bromomethyl-pyridin-2-yl)-2,2,2-trifluoro-acetamide and 1 mL of N,N-dimethylformamide. The 130 mg of trifluoroacetamide product were heated to 60° C. in a mixture of 1 mL of methanol and 4 mL of diethylamine for 3 h, then overnight at 45° C. The product was filtered off and washed with a small amount of DCM. Yield: 36 mg of a white solid: LC-MSD, m/z for C23H20N4O2 [M+H]+=385.2; HPLC retention time: 0.8 min.

Workup

  1. customovernight
  2. customat 45° C
  3. filtrationThe product was filtered off
  4. washwashed with a small amount of DCM

Sources & evidence

ORD record
ord-ead8bca681e14c00af7fb6607962ec01
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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