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N-(2-formyl-5,8-dioxo-5,8-dihydroquinolin-7-yl)acetamide → 7-N-acetyldemethyllavendamycin methyl ester

HRID 1278588
Notes
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Reaction equation

HRID 1278588 reaction equation
[C:1]([NH:4][C:5]1[C:14](=[O:15])[C:13]2[N:12]=[C:11]([CH:16]=O)[CH:10]=[CH:9][C:8]=2[C:7](=[O:18])[CH:6]=1)(=[O:3])[CH3:2].CN(C[CH2:23][O:24][C:25](=[O:39])[C@H:26]([CH:28](C)[C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31][CH:30]=1)[NH2:27])C>C1(OC)C=CC=CC=1>[CH3:2][C:1]([NH:4][C:5]1[C:14](=[O:15])[C:13]2[N:12]=[C:11]([C:16]3[N:27]=[C:26]([C:25]([O:24][CH3:23])=[O:39])[CH:28]=[C:29]4[C:37]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[NH:31][C:30]=34)[CH:10]=[CH:9][C:8]=2[C:7](=[O:18])[CH:6]=1)=[O:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 11586798N-(2-formyl-5,8-dioxo-5,8-dihydroquinolin-7-yl)acetamideHCID 54068225b-Methyltryptophan n,n-dimethylaminoethyl ester

Product 1

HCID 116621517-N-acetyldemethyllavendamycin methyl ester

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Conditions

Temperature
100 °C

Procedure

7-N-ACETYLLAVENDAMYCIN N,N-DIMETHYLAMINOETHYL ESTER (Compound 19, Table I): 7-Acetamido-2-formylquinoline-5,8-dione (23) (prepared as described in Example 23) (317 mg, 0.13 mmol) was dissolved in 16 ml of dry anisole and heated to 80° C. b-methyltryptophan N,N-dimethylaminoethyl ester (41) (prepared as described in Example 41) (37.5 mg, 0.13 mmol) was added with stirring, and the stirred mixture was heated at 100° C. for 5.5 hr. The reaction mixture was allowed to cool to room temperature and the solid was filtered. The filtrate was distilled under vacuum to dryness. Ethyl acetate (3 ml) was added, and the mixture was stirred. Upon filtration 24.5 mg (a yield of 36%) of an orange solid was obtained.

Workup

  1. additionwas added
  2. temperatureto cool to room temperature
  3. filtrationthe solid was filtered
  4. distillationThe filtrate was distilled under vacuum to dryness
  5. additionEthyl acetate (3 ml) was added
  6. stirringthe mixture was stirred
  7. filtrationUpon filtration 24.5 mg (a yield of 36%) of an orange solid
  8. customwas obtained

Sources & evidence

ORD record
ord-5e300ffaddd84793b62fdee589833880
Source dataset
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06444684B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes