3-Aminobutanoic acid--hydrogen chloride (1/1) → HCID 71736905, compound

HRID 1481085Notes

Reaction equation

HRID 1481085 reaction equation
CO[C:3]([C:5]1[N:6]=[C:7]([C:23]#[N:24])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].Cl.[NH2:26][C@@H:27]([CH3:32])[CH2:28][C:29]([OH:31])=[O:30].C[O-].[Na+]>COCCO>[C:23]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:9]=2)[C:14]([OH:15])=[C:5]([C:3]([NH:26][C@@H:27]([CH3:32])[CH2:28][C:29]([OH:31])=[O:30])=[O:4])[N:6]=1)#[N:24]

Participants

5

Reactant 3

HCID 27615053-Aminobutanoic acid--hydrogen chloride (1/1)HCID 10942334Sodium MethoxideHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 71736905HCID 71736905, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

To a mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (110 mg, 0.34 mmol) and 3-(S)-amino-butyric acid HCl salt (475 mg, 3.4 mmol) (Oakwood Products) in 2-methoxyethanol (10 mL) was added NaOMe solid (330 mg, 6.12 mmol). The resultant mixture was refluxed for 7 h. Reaction mixture was concentrated and the residue was dissolved in water (100 mL). It was acidified by 1 N HCl to pH=3-4 and then extracted with EtOAc. Organic layer was washed with water, brine and dried over MgSO4. It was filtered and concentrated. The crude product was triturated with (1/1) EtOAc/hexanes. Solid was collected and dried in vacuo to provide the title compound 52 mg (0.13 mmol) in 39% yield. LC-MS ESI−: 390.02 (M−1)−.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated
  3. dissolutionthe residue was dissolved in water (100 mL)
  4. extractionextracted with EtOAc
  5. washOrganic layer was washed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationIt was filtered
  8. concentrationconcentrated
  9. customThe crude product was triturated with (1/1) EtOAc/hexanes
  10. customSolid was collected
  11. customdried in vacuo

Sources & evidence

ORD record
ord-385eb782bd674169a1184bc9bc107527
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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