Gamma-Aminobutyric Acid → HCID 89812909, compound

HRID 1481123Notes

Reaction equation

HRID 1481123 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][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.[NH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31].C[O-].[Na+].CO>>[OH:18][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[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 23694274Sodium methanolate methanolHCID 66712741HCID 66712741, compound

Product 1

HCID 89812909HCID 89812909, compoundYield 92%

Procedure

A mixture of 4-hydroxy-6-phenoxy-isoquinoline-3-carboxylic acid butyl ester (150 mg, 0.45 mmol) and 4-amino-butyric acid (688 mg, 6.68 mmol) in 0.5 M NaOMe/MeOH (8.9 mL, 4.45 mmol) was refluxed overnight. Reaction mixture was concentrated and residue was dissolved in water (150 mL). It was acidified by 1 N HCl to pH=3-4. Precipitate was collected, rinsed with water and dried in vacuo to provide the title compound 151 mg (0.41 mmol) in 92% yield. LC-MS ESI−: 365.08 (M−1)−.

Workup

  1. temperaturewas refluxed overnight
  2. customReaction mixture
  3. concentrationwas concentrated
  4. dissolutionresidue was dissolved in water (150 mL)
  5. customPrecipitate was collected
  6. washrinsed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-ea9eb765e35e47a9a83bac3ef238f6ac
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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