Hydrochloric Acid → HCID 71736742, compound

HRID 1481099Notes

Reaction equation

HRID 1481099 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].[CH3:25][O-:26].[Na+].CO.Cl.[OH2:31]>>[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:6][CH2:5][C@@H:14]([CH3:13])[C:25]([OH:31])=[O:26])=[O:4])[N:6]=1)#[N:24]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23694274Sodium methanolate methanolHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 71736742HCID 71736742, compoundYield 14%

Procedure

To a mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (50 mg, 0.16 mmol) and 3-amino-2-(R)-methyl-propionic acid, trifluoroacetic acid salt (32 mg, 0.32 mmol) was added 0.5 M NaOMe/MeOH solution (1.52 mL) (to bring the pH of the mixture to 8). The resultant mixture was microwaved at 130° C. for 1 h. Reaction mixture was diluted with water (80 mL) and acidified by 1 N HCl to pH=3-4. It was extracted with EtOAc. Organic layer was washed with brine, dried over MgSO4, filtered and concentrated. Crude product was purified by silica gel chromatography, eluting with 5-100% EtOAc/CH2Cl2, to provide the title compound 8.6 mg (0.022 mmol) in 14% yield. LC-MS ESI−: 390.12 (M−1)−.

Workup

  1. customReaction mixture
  2. extractionIt was extracted with EtOAc
  3. washOrganic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customCrude product was purified by silica gel chromatography
  8. washeluting with 5-100% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-08bfb751f2564a6dad8b4783855c6240
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

Loading…