Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate → HCID 117843666, compound

HRID 1480988Notes

Reaction equation

HRID 1480988 reaction equation
C[O:2][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.[C:25]([O:29][C:30]([C:32]1([CH2:39][NH2:40])[CH2:37][CH2:36][S:35](=[O:38])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>CCO>[C:25]([O:29][C:30]([C:32]1([CH2:39][NH:40][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:2])[CH2:33][CH2:34][S:35](=[O:38])[CH2:36][CH2:37]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylateHCID 117844066HCID 117844066, compound

Product 1

HCID 117843666HCID 117843666, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-cyano-1-oxo-hexahydro-1λ4-thiopyran-4-carboxylic acid tert-butyl ester (193 mg) and Raney Ni (0.5 mL in water) in MeOH (30 mL) was stirred at rt under H2 atmosphere (balloon) overnight. Then the reaction mixture was filtered over Celite pad, filtrate was concentrated to give the desired product 4-aminomethyl-1-oxo-hexahydro-1λ4-thiopyran-4-carboxylic acid tert-butyl ester (195 mg), which was used in the next step. A mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (35 mg) and 4-aminomethyl-1-oxo-hexahydro-1λ4-thiopyran-4-carboxylic acid tert-butyl ester (52 mg) in EtOH (1.5 mL) was refluxed overnight. The mixture was cooled, concentrated and the residue was column purified to give the desired product (23 mg). LC MS ESI+: 536 (M+1)+.

Workup

  1. temperaturewas refluxed overnight
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. custompurified

Sources & evidence

ORD record
ord-b69cdf0fb8f14a22a0af72ecbb3c9eda
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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