(+/-)-4-Aminopentanoic acid → HCID 89813151, compound

HRID 1481239Notes

Reaction equation

HRID 1481239 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].[NH2:25][CH:26]([CH3:32])[CH2:27][CH2:28][C:29]([OH:31])=[O:30]>C[O-].[Na+].CO>[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:25][CH:26]([CH3:32])[CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:4])[N:6]=1)#[N:24]

Participants

5

Reactant 2

HCID 223130(+/-)-4-Aminopentanoic acidHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 89813151HCID 89813151, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

A mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (50 mg, 0.16 mmole) and 4-amino-pentanoic acid (prepared from hydrolysis of 5-methyl-2-pyrrolidinone in 6 N HCl at reflux for 2 days, followed by lyophilization, 274 mg, 2.4 mmole) in 0.5 M sodium methoxide in methanol (4.6 ml) was refluxed for twenty hours before it was cooled to room temperature, concentrated and dissolved in water, extracted with dichloromethane. The remaining aqueous layer was acidified with 1N hydrochloric chloride, extracted with a mixture of dichloromethane and methanol. The organic layer was dried over anhydrous sodium sulfate, concentrated and purified by flash column chromatography on silica gel with a gradient of dichloromethane and methanol to give the title compound as a white solid (43 mg). LC-MS ESI−: 404 (M−1)−.

Workup

  1. temperaturewas refluxed for twenty hours before it
  2. concentrationconcentrated
  3. dissolutiondissolved in water
  4. extractionextracted with dichloromethane
  5. extractionextracted with a mixture of dichloromethane and methanol
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. custompurified by flash column chromatography on silica gel with a gradient of dichloromethane and methanol

Sources & evidence

ORD record
ord-f49e2d82ee5a4cd199631f971d75931b
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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