Diethylamine → 1-(6-Amino-pyridin-2-ylmethyl)-3-(4-methoxy-3-methyl-benzoyl)-1H-quinolin-4-one

HRID 227008Notes

Reaction equation

HRID 227008 reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:23])[C:15]([C:24](=[O:34])[C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([CH3:33])[CH:26]=3)=[CH:14]2)[N:7]=1)=O.C(NCC)C>CO>[NH2:5][C:6]1[N:7]=[C:8]([CH2:12][N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:23])[C:15]([C:24](=[O:34])[C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([CH3:33])[CH:26]=3)=[CH:14]2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 577547792,2,2-Trifluoro-N-{6-[3-(4-methoxy-3-methyl-benzoyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridin-2-yl}-acetamide

Product 1

HCID 577545401-(6-Amino-pyridin-2-ylmethyl)-3-(4-methoxy-3-methyl-benzoyl)-1H-quinolin-4-oneYield 18.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 212 mg (0.43 mmol) 2,2,2-Trifluoro-N-{6-[3-(4-methoxy-3-methyl-benzoyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridin-2-yl}-acetamide, excess diethylamine and 5 mL of methanol were heated at 45° C. overnight. The solid was collected by filtration and purified by reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA to yield 32.4 mg of 1-(6-Amino-pyridin-2-ylmethyl)-3-(4-methoxy-3-methyl-benzoyl)-1H-quinolin-4-one. LC-MSD, m/z for C24H21N3O3 [M+H]: 400.16 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 1.5 min.

Workup

  1. filtrationThe solid was collected by filtration
  2. custompurified by reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA

Sources & evidence

ORD record
ord-c03eda2a2dc748e7a17b995b9729c44d
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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