Hydrochloric Acid → HCID 71735136, compound

HRID 1480932Notes

Reaction equation

HRID 1480932 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][CH2:24][C:25]([CH3:30])([CH3:29])[C:26]([OH:28])=[O:27].CO.Cl>C[O-].[Na+].O>[OH:15][C:14]1[C:13]2[C:8](=[CH:9][C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:11][CH:12]=2)[CH:7]=[N:6][C:5]=1[C:3]([NH:23][CH2:24][C:25]([CH3:30])([CH3:29])[C:26]([OH:28])=[O:27])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 957392,2-Dimethyl-beta-alanineHCID 86709142Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 71735136HCID 71735136, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10942334Sodium MethoxideSolvent

Procedure

A mixture of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (68 mg, 0.23 mmol) and 3-amino-2,2-dimethyl-propionic acid (81 mg, 0.69 mmol) (ChemBridge) in 0.5 N NaOMe in MeOH solution (0.92 mL, 0.46 mmol) was microwaved at 120° C. for 1 h. Reaction mixture was diluted with water (50 mL) and acidified by 1 N HCl solution to pH=3-4. Precipitate was collected and rinsed with water and dried in vacuo to provide the title compound (71 mg, 0.19 mmol) as an off-white solid in 81% yield. LC-MS ESI−: 379.04 (M−1)−.

Workup

  1. customwas microwaved at 120° C. for 1 h
  2. customReaction mixture
  3. customPrecipitate was collected
  4. washrinsed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-16ecc34d6cc14e71ab1602e6fa35cf3e
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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