HCID 178471916, compound → 3-(5,6-Dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-one

HRID 226928Notes

Reaction equation

HRID 226928 reaction equation
C(O[C:4](=[O:24])[C:5]([C:14]([C:16]1[CH:17]=[N:18][C:19]([CH3:23])=[C:20]([CH3:22])[CH:21]=1)=[O:15])=[CH:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:22][C:20]1[CH:21]=[C:16]([C:14]([C:5]2[C:4](=[O:24])[C:9]3[C:8](=[CH:13][CH:12]=[CH:11][CH:10]=3)[NH:7][CH:6]=2)=[O:15])[CH:17]=[N:18][C:19]=1[CH3:23]

Participants

3

Reactant 1

HCID 178471916HCID 178471916, compound

Product 1

HCID 577545393-(5,6-Dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-oneYield 58.7%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Compound 3c was prepared following the procedure described in Step 2 of Example 1 using 400 mg (1.23 mmol) of 2-(5,6-dimethyl-pyridine-3-carbonyl)-3-phenylamino-acrylic acid ethyl ester 2d, and 50 mL of diphenyl ether. The reaction time was 1 h. Purification of the crude product by flash chromatography using 60-100% ethyl acetate in hexane followed by 0-25% methanol in ethyl acetate yielded 201 mg of the product 3c as off-white solid: LC-MSD, m/z for C17H14N2O2 [M+H]+=279.4, HPLC retention time: 0.25 min.

Workup

  1. customCompound 3c was prepared
  2. customPurification of the crude product by flash chromatography

Sources & evidence

ORD record
ord-61b4a5567cf8480681d81857431cd841
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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