5-Aminovaleric acid → 5-[(4-Hydroxy-7-phenylamino-isoquinoline-3-carbonyl)-amino]-pentanoic acid

HRID 1481142Notes

Reaction equation

HRID 1481142 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:10]=2)[CH:5]=[N:4][C:3]=1[C:19](OC)=[O:20].[NH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29].C[O-].[Na+].CO>>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:10]=2)[CH:5]=[N:4][C:3]=1[C:19]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:20]

Participants

5

Reactant 4

HCID 1385-Aminovaleric acidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 89812927HCID 89812927, compound

Product 1

HCID 717361025-[(4-Hydroxy-7-phenylamino-isoquinoline-3-carbonyl)-amino]-pentanoic acid

Procedure

A mixture of methyl 4-hydroxy-7-(phenylamino)isoquinoline-3-carboxylate (30.0 mg, 0.09 mmol), 5-aminovaleric acid (216.3 mg, 1.9 mmol, Sigma-Aldrich) and NaOMe in MeOH (2.8 mL, 1.4 mmol, 0.5 M solution, Sigma-Aldrich) was heated to reflux for 20 hours before cooling to room temperature. The solvent was removed in vacuo and the residue was dissolved in H2O (10 mL) and EtOAc (10 mL). To the stirred mixture was added 1 N hydrochloric acid until pH was 1. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography (0-30% MeOH/CH2Cl2) to give the title compound in 27 mg. MS: (+) m/z 380.11 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in H2O (10 mL)
  5. additionTo the stirred mixture was added 1 N hydrochloric acid until pH was 1
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted twice with EtOAc
  8. dry with materialThe combined organic layers were dried over MgSO4
  9. concentrationconcentrated
  10. custompurified by flash chromatography (0-30% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f82d885a09dd475dae0ae60199e267c3
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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