Ethyl Acetate → [(1-Dimethylcarbamoyl-4-hydroxy-isoquinoline-3-carbonyl)-amino]-acetic acid

HRID 523799Notes

Reaction equation

HRID 523799 reaction equation
C([O:8][C:9](=[O:37])[CH2:10][NH:11][C:12]([C:14]1[N:15]=[C:16]([C:32](=[O:36])[N:33]([CH3:35])[CH3:34])[C:17]2[C:22]([C:23]=1[O:24]CC1C=CC=CC=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:13])C1C=CC=CC=1.CCOC(C)=O>[Pd].CO>[CH3:34][N:33]([CH3:35])[C:32]([C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:23]([OH:24])=[C:14]([C:12]([NH:11][CH2:10][C:9]([OH:37])=[O:8])=[O:13])[N:15]=1)=[O:36]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 66712806[(4-Benzyloxy-1-dimethylcarbamoyl-isoquinoline-3-carbonyl)-amino]-acetic acid benzyl ester

Product 1

HCID 11438497[(1-Dimethylcarbamoyl-4-hydroxy-isoquinoline-3-carbonyl)-amino]-acetic acidYield 91.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of [(4-Benzyloxy-1-dimethylcarbamoyl-isoquinoline-3-carbonyl)-amino]-acetic acid benzyl ester (209 mg, 0.42 mmol), Pd/C (100 mg, 10 wt % Pd), EtOAc (10 ml) and MeOH (50 ml) was stirred under a H2-atmosphere at ambient pressure and temperature for 18 h. Then the mixture was filtered through a pad of celite. Celite and filter cake were washed thoroughly with EtOAc and the combined organic phases were concentrated in vacuo to give the title compound as a brown solid (122 mg); MS-(−)-ion: M−1=316.1.

Workup

  1. filtrationThen the mixture was filtered through a pad of celite
  2. filtrationCelite and filter cake
  3. washwere washed thoroughly with EtOAc
  4. concentrationthe combined organic phases were concentrated in vacuo

Sources & evidence

ORD record
ord-82101fea534f419683e6bc942c635a51
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Reaction notes

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