HCID 81947339, compound → HCID 89812957, compound

HRID 1481050Notes

Reaction equation

HRID 1481050 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:20])=[C:5]([C:21](OC)=[O:22])[N:4]=1)#[N:2].[C:25]([O:29][C:30](=[O:37])[C:31]([CH2:35][NH2:36])([CH3:34])[CH2:32][CH3:33])([CH3:28])([CH3:27])[CH3:26]>CO>[C:25]([O:29][C:30](=[O:37])[C:31]([CH2:35][NH:36][C:21]([C:5]1[N:4]=[C:3]([C:1]#[N:2])[C:12]2[C:7]([C:6]=1[OH:20])=[CH:8][CH:9]=[C:10]([O:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH:11]=2)=[O:22])([CH3:34])[CH2:32][CH3:33])([CH3:26])([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 81947339HCID 81947339, compoundHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 89812957HCID 89812957, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate (55 mg, 0.17 mmol) and 2-aminomethyl-2-methyl-butyric acid tert-butyl ester (88 mg of the crude, 0.47 mmol) in MeOH (3 mL) were heated at 140° C. in a microwave for 1 hour. The solvent was removed in vacuo and the residue oil was purified by flash chromatography (0-50% EtOAc/hexanes) to give the title compound in 60 mg. MS: (−) m/z 474.24 (M−1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue oil was purified by flash chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-06401546aacb4221b396888b091652a9
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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