Methyl chloroglyoxylate → HCID 66816087, compound

HRID 1697102Notes

Reaction equation

HRID 1697102 reaction equation
CS([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([C:15]2[C:16]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=3)=[N:17][C:18]([CH3:21])=[CH:19][CH:20]=2)=[O:14])=[CH:7][CH:6]=1)(=O)=O.[CH3:32][O:33][C:34](=[O:38])[C:35](Cl)=O>C1COCC1>[CH3:32][O:33][C:34]([C:35]1[N:22]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)[C:16]2[C:15]([C:13](=[O:14])[C:12]=1[CH2:11][C:8]1[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=1)=[CH:20][CH:19]=[C:18]([CH3:21])[N:17]=2)=[O:38]

Participants

4

Reactant 2

HCID 79846Methyl chloroglyoxylateHCID 66816344HCID 66816344, compound

Product 1

HCID 66816087HCID 66816087, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

3-(4-Methanesulfonyl-phenyl)-1-[6-methyl-2-(3-nitrophenylamino)-pyridin-3-yl]-propan-1-one (0.1 g) was dissolved in THF (5 mL). Chloro-oxo-acetic acid methyl ester (0.1 mL) was added, and the mixture heated by microwave at 80° C. for 1 h. The product was concentrated, the residue taken up in MeOH (5 mL), K2CO3 (0.1 g) added, and the mixture heated at 50° C. for 15 min. The product was cooled and concentrated, and purified by prep TLC (50% EtOAc/hexane) to provide 3-benzyl-7-methyl-1-(3-nitrophenyl)-4-oxo-1,4-dihydro[1,8]-naphthyridine-2-carboxylic acid methyl ester (Compound 104, ˜20 mg). M+H=508.

Workup

  1. concentrationThe product was concentrated
  2. additionK2CO3 (0.1 g) added
  3. temperaturethe mixture heated at 50° C. for 15 min
  4. temperatureThe product was cooled
  5. concentrationconcentrated
  6. custompurified by prep TLC (50% EtOAc/hexane)

Sources & evidence

ORD record
ord-67f2de886b0e48e993716955b5fc6766
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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