Hydrochloric Acid → HCID 89812858, compound

HRID 1480936Notes

Reaction equation

HRID 1480936 reaction equation
CO[C:3]([C:5]1[N:6]=[CH:7][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].[NH2:23][C:24]([CH3:30])([CH3:29])[CH2:25][C:26]([OH:28])=[O:27].C[O-].[Na+].Cl>CN(C=O)C.O>[OH:15][C:14]1[C:13]2[C:8](=[CH:9][C:10]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:11][CH:12]=2)[CH:7]=[N:6][C:5]=1[C:3]([NH:23][C:24]([CH3:30])([CH3:29])[CH2:25][C:26]([OH:28])=[O:27])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 27609333-Amino-3-methylbutanoic acidHCID 10942334Sodium MethoxideHCID 86709142Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 89812858HCID 89812858, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (100 mg, 0.34 mmol) and 3-amino-3-methyl-butyric acid (Oakwood) (199 mg, 1.7 mmol) in DMF (3 mL) was added sodium methoxide solid (73 mg, 1.36 mmoL). The mixture was gently refluxed for 2 h. After cooled, it was diluted with water (100 mL) and acidified by 1 N HCl aqueous solution to pH=3-4. Precipitate was collected and dried in vacuo. The crude product was purified by silica gel chromatography, eluting with 20%-100% EtOAc-hexanes, to provide the title compound (42 mg, 0.11 mmol) in 33% yield. LC-MS ESI−: 379.04 (M−1)−.

Workup

  1. temperatureThe mixture was gently refluxed for 2 h
  2. temperatureAfter cooled
  3. customPrecipitate was collected
  4. customdried in vacuo
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with 20%-100% EtOAc-hexanes

Sources & evidence

ORD record
ord-5ffec75711be421e8a541573b9af935a
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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