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

HRID 1480947Notes

Reaction equation

HRID 1480947 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].[CH3:25][O:26][C:27]([C:29]1([CH2:33][NH2:34])[CH2:32][CH2:31][CH2:30]1)=[O:28]>CO>[CH3:25][O:26][C:27]([C:29]1([CH2:33][NH:34][C:3]([C:5]2[N:6]=[C:7]([C:23]#[N:24])[C:8]3[C:13]([C:14]=2[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:9]=3)=[O:4])[CH2:32][CH2:31][CH2:30]1)=[O:28]

Participants

4

Reactant 2

HCID 25918829Methyl 1-(Aminomethyl)cyclobutanecarboxylateHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 898129681-{[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-cyclobutanecarboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After a mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (129 mg, 0.401 mmol), 1-aminomethyl-cyclobutanecarboxylic acid methyl ester (115 mg, 0.803 mmol in MeOH 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 (172 mg). LC MS ESI+: 432 (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-22c94f61ee944e43bd8fad31c8fdc65c
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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