4-Aminomethyl-tetrahydro-pyran-4-carboxylic acid methyl ester → 4-{[(4-Hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-tetrahydro-pyran-4-carboxylic acid methyl ester

HRID 1480948Notes

Reaction equation

HRID 1480948 reaction equation
CO[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:4].[CH3:23][O:24][C:25]([C:27]1([CH2:33][NH2:34])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[O:26]>CO>[CH3:23][O:24][C:25]([C:27]1([CH2:33][NH:34][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:4])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[O:26]

Participants

4

Reactant 2

HCID 254188244-Aminomethyl-tetrahydro-pyran-4-carboxylic acid methyl esterHCID 86709142Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 898129554-{[(4-Hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-tetrahydro-pyran-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After a mixture of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (121 mg), 4-aminomethyl-tetrahydro-pyran-4-carboxylic acid methyl ester (177 mg; commercially available) in MeOH (3 mL) was microwaved at 150° C. for 650 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 (48 mg). LC MS ESI+: 437 (M+1)+.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customthe residue was partitioned between EtOAc and diluted HCl solution, EtOAc phase
  4. washwas washed with water and diluted NaCl solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customcolumn purified

Sources & evidence

ORD record
ord-252c36256899450f9eeb32d83e18a9f9
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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