Methyl 1-(Aminomethyl)cyclobutanecarboxylate → 1-{[(4-Hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-cyclobutanecarboxylic acid methyl ester

HRID 1480946Notes

Reaction equation

HRID 1480946 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[CH:7][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.[CH3:23][O:24][C:25]([C:27]1([CH2:31][NH2:32])[CH2:30][CH2:29][CH2:28]1)=[O:26]>CO>[CH3:23][O:24][C:25]([C:27]1([CH2:31][NH:32][C:3]([C:5]2[N:6]=[CH:7][C:8]3[C:13]([C:14]=2[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=3)=[O:2])[CH2:30][CH2:29][CH2:28]1)=[O:26]

Participants

4

Reactant 2

HCID 25918829Methyl 1-(Aminomethyl)cyclobutanecarboxylateHCID 86709142Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 1178436821-{[(4-Hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-cyclobutanecarboxylic acid methyl esterYield 50.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (110 mg, 0.37 mmol) and 1-aminomethyl-cyclobutanecarboxylic acid methyl ester (159 mg, 1.11 mmol, available from Ukrorgsyntez Ltd) in MeOH (2 mL) was microwaved at 150° C. for 500 min; cooled, concentrated, the residue was partitioned between EtOAc and diluted HCl solution, EtOAc phase was washed with water and diluted NaCl solution, dried over anhydrous sodium sulfate, filtered, concentrated and column purified to give product (76 mg). LC MS ESI+: 407 (M+1)+.

Workup

  1. customwas microwaved at 150° C. for 500 min
  2. temperaturecooled
  3. concentrationconcentrated
  4. customthe residue was partitioned between EtOAc and diluted HCl solution, EtOAc phase
  5. washwas washed with water and diluted NaCl solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customcolumn purified

Sources & evidence

ORD record
ord-effa3885ea85486787179204f02a4ba1
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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