Hydrochloric Acid → HCID 71736745, compound

HRID 1481089Notes

Reaction equation

HRID 1481089 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][C:26]([CH3:32])([CH3:31])[CH2:27][C:28]([OH:30])=[O:29].C[O-].[Na+].Cl>CN(C=O)C.O>[C:23]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:9]=2)[C:14]([OH:15])=[C:5]([C:3]([NH:25][C:26]([CH3:32])([CH3:31])[CH2:27][C:28]([OH:30])=[O:29])=[O:4])[N:6]=1)#[N:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 27609333-Amino-3-methylbutanoic acidHCID 10942334Sodium MethoxideHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 71736745HCID 71736745, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (100 mg, 0.31 mmol) and 3-amino-3-methyl-butyric acid ((97 mg, 0.94 mmol) (Oakwood) in DMF (3 mL) was added NaOMe solid (68 mg, 1.25 mmol). The resultant mixture was heated in a 150-160° C. oil bath for 3 h. Reaction mixture was diluted with water (100 mL) and acidified by 1 N HCl to pH=3-4. Precipitate was collected and dried. Crude residue was purified by silica gel chromatography, eluting with 10-50% EtOAc/CH2Cl2. Fractions containing the produce were collected and concentrated. It was triturated with MeOH (2 mL). Solid was collected and dried in vacuo to provide the title compound 51 mg (0.13 mmol) in 41% yield. LC-MS ESI−: 404.06 (M−1)−.

Workup

  1. customReaction mixture
  2. customPrecipitate was collected
  3. customdried
  4. customCrude residue was purified by silica gel chromatography
  5. washeluting with 10-50% EtOAc/CH2Cl2
  6. additionFractions containing the produce
  7. customwere collected
  8. concentrationconcentrated
  9. customIt was triturated with MeOH (2 mL)
  10. customSolid was collected
  11. customdried in vacuo

Sources & evidence

ORD record
ord-d8a7d09a168b4bc0abe03228a7190fa7
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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