Acetic Acid → HCID 60150991, compound

HRID 919763Notes

Reaction equation

HRID 919763 reaction equation
CO[C:3]([C:5]1[N:6]=[C:7]([C:24]#[N:25])[C:8]2[C:9](=[O:23])[N:10]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:4].[N:26]1([CH2:32][CH2:33][NH2:34])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.CC(O)=O.O>CCO>[N:26]1([CH2:32][CH2:33][NH:34][C:3]([C:5]2[N:6]=[C:7]([C:24]#[N:25])[C:8]3[C:9](=[O:23])[N:10]([CH2:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:11]=[CH:12][C:13]=3[C:14]=2[OH:15])=[O:4])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4082852-MorpholinoethylamineHCID 682976087-Benzyl-1-cyano-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

Product 1

HCID 60150991HCID 60150991, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-benzyl-1-cyano-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (25 mg, 0.075 mmol) and 2-morpholin-4-yl-ethylamine (0.034 mL, 0.26 mmol) in EtOH (2 mL) was refluxed for 16 h. After the mixture was cooled to r.t., AcOH (0.1 mL) and water (5 mL) were added. The resulting mixture was extracted with EtOAc, and the organic layer was dried over MgSO4 and concentrated. The crude product was purified by chromatography (0-10% MeOH/CH2Cl2) to give 18 mg of the title compound. MS: (+) m/z 434.34 (M+1).

Workup

  1. temperaturewas refluxed for 16 h
  2. extractionThe resulting mixture was extracted with EtOAc
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-5829e1c24c764eba969b049d83d5e411
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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