Hydrochloric Acid → HCID 71736595, compound

HRID 1481107Notes

Reaction equation

HRID 1481107 reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]([C:26]#[N:27])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[Cl:25])[CH:10]=2)=[O:5])C.Cl.[OH2:29]>C[O-].[Na+].CO>[Cl:25][C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[O:17][C:11]1[CH:10]=[C:9]2[C:14]([C:15]([OH:16])=[C:6]([C:4]([NH:27][CH2:26][CH2:8][CH2:9][CH2:10][C:11]([OH:17])=[O:29])=[O:5])[N:7]=[C:8]2[C:26]#[N:27])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 89813167HCID 89813167, compound

Product 1

HCID 71736595HCID 71736595, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 1-cyano-4-hydroxy-7-(4-fluoro-2-chloro-phenoxy)-isoquinoline-3-carboxylic acid ethyl ester (50 mg, 0.13 mmol) and 5-amino-petanoic acid (45 mg, 0.39 mmol) in 0.5 M NaOMe/MeOH solution was microwaved at 130° C. for 1 h. Reaction mixture was diluted with water (60 mL) and acidified by 1 N HCl to pH=3-4. Precipitate was collected and dried. Crude product was then purified by silica gel chromatography, eluting with 5-70% EtOAc/hexanes to provide the title compound 27 mg (0.06 mmol) in 45% yield. LC-MS ESI−: 455.89 (M−1)−.

Workup

  1. customwas microwaved at 130° C. for 1 h
  2. customReaction mixture
  3. customPrecipitate was collected
  4. customdried
  5. customCrude product was then purified by silica gel chromatography
  6. washeluting with 5-70% EtOAc/hexanes

Sources & evidence

ORD record
ord-03f54ac84db34b448c4854a35da48bfc
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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