Gamma-Aminobutyric Acid → HCID 71735943, compound

HRID 1481125Notes

Reaction equation

HRID 1481125 reaction equation
C(O[C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])CCC.[NH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31].C[O-].[Na+]>>[OH:18][C:17]1[C:16]2[C:11](=[CH:12][C:13]([S:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9][C:8]=1[C:6]([NH:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[O:7]

Participants

4

Reactant 3

HCID 119Gamma-Aminobutyric AcidHCID 10942334Sodium MethoxideHCID 667130924-Hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 71735943HCID 71735943, compoundYield 91.5%

Procedure

A mixture of 4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester (50 mg, 0.14 mmol) (prepared according to WO 2004108681), 4-aminobutyric acid (730 mg, 7.08 mmol) and NaOMe (11 mL, 5.31 mmol, 0.5 M in MeOH) was refluxed for 3 days, then partitioned between EtOAc and water. 1 M HCl was added with stirring until pH was ˜1. 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 49 mg of the title compound. MS: (+) m/z 383.09 (M+1).

Workup

  1. temperaturewas refluxed for 3 days
  2. custompartitioned between EtOAc and water
  3. addition1 M HCl was added
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (0-60% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record
ord-6dd969eca41c496ba7ecafcf1e469b66
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

Loading…