Triethylamine → HCID 71737227, compound

HRID 1481074Notes

Reaction equation

HRID 1481074 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 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylateHCID 89813006HCID 89813006, compound

Product 1

HCID 71737227HCID 71737227, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of (2S,3S)-3-amino-2-methyl-butyric acid tert-butyl ester (20 mg, 0.12 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 taken up 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 11.1 mg of the title compound as a white 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. washwashed several times with ether
  8. extractionextracted with EtOAc
  9. dry with materialThe organic layer was dried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9be7343686d048df8c712de3bc7ff22d
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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