Acetic Acid → HCID 490485, compound

HRID 1068050Notes

Reaction equation

HRID 1068050 reaction equation
[NH2:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][CH2:14][OH:15])=[CH:9][CH:10]=2)[C:5](=[O:16])[C:4]([C:17]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[O:18])=[CH:3]1.C(O)(=O)C>CO.CN(C=O)C.[Pt]>[NH2:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][CH2:13][CH2:14][OH:15])=[CH:9][CH:10]=2)[C:5](=[O:16])[C:4]([C:17]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[O:18])=[CH:3]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 490484HCID 490484, compound

Product 1

HCID 490485HCID 490485, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

1-Amino-N-(4-chlorobenzyl)-6-(3-hydroxy-1-propynyl)-4-oxo-1,4-dihydro-3-quinolinecarboxamide (0.21 g) from Example No. 118 is dissolved in a 1:1 mixture of methanol/DMF. To the solution is added 5% platinum on carbon (0.11 g) and acetic acid (0.5 mL). The reaction is shaken under a hydrogen atmosphere (35 psi) for 4.5 hours. The catalyst is removed by filtration through Celite. The filtrate is concentrated in vacuo, and the resulting white solid is triturated with dichloromethane. The crude product is then purified by column chromatography (MeOH/CH2Cl2: 3%, 5%) yielding 0.10 g of the title compound as a white solid.

Workup

  1. customThe catalyst is removed by filtration through Celite
  2. concentrationThe filtrate is concentrated in vacuo
  3. customthe resulting white solid is triturated with dichloromethane
  4. customThe crude product is then purified by column chromatography (MeOH/CH2Cl2: 3%, 5%)

Sources & evidence

ORD record
ord-7387fc97fdb24a009756dccc61bcb8b4
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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