Hydrochloric Acid → 3-(1-Cyano-4-hydroxy-7-(4methoxyphenoxy)isoquinoline-3-carboxamido)-3-methylbutanoic acid

HRID 1480960Notes

Reaction equation

HRID 1480960 reaction equation
CO[C:3]([C:5]1[N:6]=[C:7]([C:25]#[N:26])[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][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[NH2:27][C:28]([CH3:34])([CH3:33])[CH2:29][C:30]([OH:32])=[O:31].C[O-].[Na+].Cl>CC(N(C)C)=O.O>[C:25]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:16][C:17]3[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)[CH:9]=2)[C:14]([OH:15])=[C:5]([C:3]([NH:27][C:28]([CH3:34])([CH3:33])[CH2:29][C:30]([OH:32])=[O:31])=[O:4])[N:6]=1)#[N:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 27609333-Amino-3-methylbutanoic acidHCID 10942334Sodium MethoxideHCID 898132171-Cyano-4-hydroxy-7-(4-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl ester

Product 1

HCID 898128663-(1-Cyano-4-hydroxy-7-(4methoxyphenoxy)isoquinoline-3-carboxamido)-3-methylbutanoic acidYield 21.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of 1-cyano-4-hydroxy-7-(4-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl ester (100 mg) and 3-amino-3-methyl-butyric acid (100 mg) and NaOMe (45 mg) in DMA (1.5 mL) was microwaved at 150° C. for 3 h. The mixture was cooled, diluted with water, acidified with 2 M HCl solution, solids were collected with filtration, washed with water, air dried then the residue was further column purified to give the desired product (27 mg). LC MS ESI+: 436 (M+1)+.

Workup

  1. customwas microwaved at 150° C. for 3 h
  2. temperatureThe mixture was cooled
  3. filtrationwere collected with filtration
  4. washwashed with water, air
  5. customdried
  6. custompurified

Sources & evidence

ORD record
ord-027b42c33085474d978f4a47907b90f4
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

Loading…