Triethylamine → HCID 71737229, compound

HRID 1481069Notes

Reaction equation

HRID 1481069 reaction equation
C([O:5][C:6](=[O:12])[C@H:7]([CH3:11])[C@H:8]([NH2:10])[CH3:9])(C)(C)C.C[O:14][C:15]([C:17]1[N:18]=[C:19]([C:35]#[N:36])[C:20]2[C:25]([C:26]=1[OH:27])=[CH:24][CH:23]=[C:22]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:21]=2)=O.C(N(CC)CC)C>CCO>[C:35]([C:19]1[C:20]2[C:25](=[CH:24][CH:23]=[C:22]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:21]=2)[C:26]([OH:27])=[C:17]([C:15]([NH:10][C@H:8]([CH3:9])[C@@H:7]([CH3:11])[C:6]([OH:5])=[O:12])=[O:14])[N:18]=1)#[N:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10103638HCID 10103638, compoundHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 71737229HCID 71737229, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of (2R,3R)-3-amino-2-methyl-butyric acid tert-butyl ester (20 mg, 0.117 mmol), 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (25 mg, 0.078 mmol), and triethylamine (0.050 mL) in EtOH (2 mL) was heated in a microwave reactor at 140° C. for 6 h. The resulting mixture was concentrated to dryness, and the residue was re-dissolved in CH2Cl2 and passed through a plug of silica gel. After evaporating the solvent, the residue was dissolved in CH2Cl2 (3 mL) and treated with trifluoroacetic acid (2 mL) for 2 h. The mixture was concentrated in vacuo, and the resulting residue was dissolved in saturated NaHCO3 and washed several times with ether. The aqueous layer was acidified to pH ˜2 and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give 9.4 mg of the title compound as a pale pink solid. MS: (−) m/z 404.32 (M−1).

Workup

  1. concentrationThe resulting mixture was concentrated to dryness
  2. dissolutionthe residue was re-dissolved in CH2Cl2
  3. customAfter evaporating the solvent
  4. dissolutionthe residue was dissolved in CH2Cl2 (3 mL)
  5. additiontreated with trifluoroacetic acid (2 mL) for 2 h
  6. concentrationThe mixture was concentrated in vacuo
  7. dissolutionthe resulting residue was dissolved in saturated NaHCO3
  8. washwashed several times with ether
  9. extractionextracted with EtOAc
  10. dry with materialThe organic layer was dried over MgSO4
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-2fab732a96a24c3cbbfbc6adc85364b6
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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