Hydrochloric Acid → HCID 89812850, compound

HRID 1481090Notes

Reaction equation

HRID 1481090 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].[NH2:25][CH2:26][CH2:27][C@H:28]([OH:32])[C:29]([OH:31])=[O:30].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:25][CH2:26][CH2:27][C@H:28]([OH:32])[C:29]([OH:31])=[O:30])=[O:4])[N:6]=1)#[N:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 27339294-Amino-2-hydroxybutyric acid, (S)-(-)-HCID 23694274Sodium methanolate methanolHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 89812850HCID 89812850, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (100 mg, 0.31 mmol) and 4-amino-2-(S)-hydroxy-butyric acid (112 mg, 0.94 mmol) (Aldrich) in 0.5 M NaOMe/MeOH (1.25 mL, 0.63 mmol) was microwaved at 120° C. for 1 h. Reaction mixture was diluted with water (60 mL), acidified by 1 N HCl to pH=3-4 and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated to provide the title compound 119 mg (0.29 mmol) in 93% yield. LC-MS ESI−: 406.00 (M−1)−.

Workup

  1. customwas microwaved at 120° C. for 1 h
  2. customReaction mixture
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6dd230de89e743b29b9753aa32e6d5d4
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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