5-Aminovaleric acid → HCID 71736594, compound

HRID 1481121Notes

Reaction equation

HRID 1481121 reaction equation
C(O[C:6]([C:8]1[N:9]=[C:10]([C:28]#[N:29])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:27])=[CH:13][CH:12]=2)=[O:7])CCC.[NH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36].C[O-].[Na+]>COCCO>[C:28]([C:10]1[C:11]2[C:16](=[CH:15][C:14]([O:19][C:20]3[C:21]([CH3:27])=[CH:22][CH:23]=[CH:24][C:25]=3[CH3:26])=[CH:13][CH:12]=2)[C:17]([OH:18])=[C:8]([C:6]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[O:7])[N:9]=1)#[N:29]

Participants

5

Reactant 3

HCID 1385-Aminovaleric acidHCID 10942334Sodium MethoxideHCID 67110152HCID 67110152, compound

Product 1

HCID 71736594HCID 71736594, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 1-cyano-6-(2,6-dimethyl-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (80 mg, 0.20 mmol), 5-aminovaleric acid (480 mg, 4.10 mmol) and NaOMe (166 mg, 3.07 mmol) in 2-methoxyethanol (10 mL) was refluxed for 2 h. After the mixture was cooled to r.t., solvent was evaporated. The residue was partitioned between EtOAc (50 mL) and water (50 mL). 1 M HCl was added with vigorous stirring until pH was ˜2. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography (0-60% EtOAc/hexanes+2% AcOH) to give 67 mg of the title compound as a pale pink solid. MS: (+) m/z 434.18 (M+1).

Workup

  1. temperaturewas refluxed for 2 h
  2. customsolvent was evaporated
  3. customThe residue was partitioned between EtOAc (50 mL) and water (50 mL)
  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 column chromatography (0-60% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record
ord-7ae7b6d6987c430b8f4a7433a53812a1
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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