5-Aminovaleric acid → HCID 89812924, compound

HRID 1481152Notes

Reaction equation

HRID 1481152 reaction equation
C(O[C:6]([C:8]1[N:9]=[C:10]([C:26]#[N:27])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:13][CH:12]=2)=[O:7])CCC.[NH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34].C[O-].[Na+]>COCCO>[C:26]([C:10]1[C:11]2[C:16](=[CH:15][C:14]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:13][CH:12]=2)[C:17]([OH:18])=[C:8]([C:6]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:7])[N:9]=1)#[N:27]

Participants

5

Reactant 3

HCID 1385-Aminovaleric acidHCID 10942334Sodium MethoxideHCID 67110485HCID 67110485, compound

Product 1

HCID 89812924HCID 89812924, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 1-cyano-4-hydroxy-6-phenoxy-isoquinoline-3-carboxylic acid butyl ester (60 mg, 0.17 mmol) (prepared according to U.S. Pat. No. 7,928,120), 5-aminovaleric acid (970 mg, 8.28 mmol) and NaOMe (360 mg, 6.62 mmol) in 2-methoxyethanol (15 mL) was refluxed for 1.5 h. Solvent was evaporated, and the residue was partitioned between EtOAc and water. 1 M HCl was added with stirring until pH was ˜2. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by preparative TLC (40% EtOAc/hexanes+2% AcOH) to give 33 mg of the title compound. MS: (+) m/z 406.13 (M+1).

Workup

  1. customprepared
  2. customSolvent was evaporated
  3. customthe residue was partitioned between EtOAc and water
  4. addition1 M HCl was added
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified by preparative TLC (40% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record
ord-c7a622602ac243a0ba06cef2175157aa
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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