HCID 53407162, compound → HCID 89812839, compound

HRID 1480956Notes

Reaction equation

HRID 1480956 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([CH2:37][NH2:38])[CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>CO>[C:25]([O:29][C:30]([C:32]1([CH2:37][NH:38][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])[CH2:33][CH2:34][CH2:35][CH2:36]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 53407162HCID 53407162, compoundHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 89812839HCID 89812839, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (200 mg) and 1-aminomethyl-cyclopentanecarboxylic acid tert-butyl ester (250 mg, commercially available from J & W PharmLab LLC, Levittown Pa.) in MeOH (3 mL) was heated at 100° C. in an oil bath for 24 h. The mixture was cooled, concentrated and the residue was column purified to give the desired product (164 mg). LC MS ESI+: 488 (M+1)+.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. custompurified

Sources & evidence

ORD record
ord-6d846ba34b8644229fa0fa38ebb658b9
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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