4-Aminomethyl-tetrahydro-pyran-4-carboxylic acid methyl ester → 4-{[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-tetrahydro-pyran-4-carboxylic acid methyl ester

HRID 1480949Notes

Reaction equation

HRID 1480949 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([CH2:35][NH2:36])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)=[O:28]>CO>[CH3:25][O:26][C:27]([C:29]1([CH2:35][NH:36][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:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=3)=[O:4])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)=[O:28]

Participants

4

Reactant 2

HCID 254188244-Aminomethyl-tetrahydro-pyran-4-carboxylic acid methyl esterHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 1178441914-{[(1-Cyano-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 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (151 mg), 4-aminomethyl-tetrahydro-pyran-4-carboxylic acid methyl ester (205 mg; commercially available) 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 (154 mg). LC MS ESI+: 462 (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-8753d281e769480393c5d5f62136bf5e
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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