Hydrochloric Acid → HCID 89813050, compound

HRID 1481101Notes

Reaction equation

HRID 1481101 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].Cl.[NH2:26][CH2:27][CH2:28][CH2:29][C:30]([CH3:35])([CH3:34])[C:31]([OH:33])=[O:32].C[O-].[Na+].CO.Cl>O>[C:23]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:9]=2)[C:14]([OH:15])=[C:5]([C:3]([NH:26][CH2:27][CH2:28][CH2:29][C:30]([CH3:35])([CH3:34])[C:31]([OH:33])=[O:32])=[O:4])[N:6]=1)#[N:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 23694274Sodium methanolate methanolHCID 717573121423034-72-3HCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 89813050HCID 89813050, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (80 mg, 0.25 mmol) and 5-Amino-2,2-dimethyl-pentanoic acid HCl salt (136 mg, 0.75 mmol) in 0.5 M NaOMe/MeOH (2.5 mL, 5 mmol) was microwaved at 120° C. for 2.5 h. Reaction mixture was diluted with water (100 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 10-100% EtOAc/hexanes to provide the title compound 17 mg (0.04 mmol) in 16% yield. LC-MS ESI−: 431.94 (M−1)−.

Workup

  1. customwas microwaved at 120° C. for 2.5 h
  2. customReaction mixture
  3. extractionIt was extracted with EtOAc
  4. washOrganic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customCrude product was purified by silica gel chromatography
  9. washeluting with 10-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-b89581f3c4e343febf9c85ffa478900e
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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