Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate → HCID 117844227, compound

HRID 1480986Notes

Reaction equation

HRID 1480986 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].[C:25]([O:29][C:30]([C:32]1([CH2:40][NH2:41])[CH2:37][CH2:36][S:35](=[O:39])(=[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([CH2:40][NH:41][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])[CH2:33][CH2:34][S:35](=[O:38])(=[O:39])[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 117843792HCID 117843792, compound

Product 1

HCID 117844227HCID 117844227, compoundYield 12.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-cyano-1,1-dioxo-hexahydro-1λ6-thiopyran-4-carboxylic acid tert-butyl ester (208 mg) and Raney Ni (0.5 mL in water) in MeOH (20 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-1,1-dioxo-hexahydro-1λ6-thiopyran-4-carboxylic acid tert-butyl ester (212 mg), which was used in the next step. A mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (24 mg) and 4-aminomethyl-1,1-dioxo-hexahydro-1λ6-thiopyran-4-carboxylic acid tert-butyl ester (45 mg) in EtOH (1 mL) was microwaved at 140° C. for 2 h. The mixture was cooled, concentrated and the residue was column purified to give the desired product (5 mg). LC MS ESI+: 552 (M+1)+.

Workup

  1. customwas microwaved at 140° C. for 2 h
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. custompurified

Sources & evidence

ORD record
ord-70d49d9df7fb4105a5e39a97307a3fca
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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