120686-17-1 → HCID 89815835, compound

HRID 1481066Notes

Reaction equation

HRID 1481066 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](=[O:41])[CH2:31][C@@H:32]([NH2:40])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH3:28])([CH3:27])[CH3:26]>COCCO>[C:25]([O:29][C:30](=[O:41])[CH2:31][C@@H:32]([NH:40][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:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH:9]=2)=[O:4])[CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 2

HCID 1501868120686-17-1HCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 89815835HCID 89815835, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (40 mg, 0.125 mmol) and (S)-3-amino-4-phenyl-butyric acid tert-butyl ester (88 mg, 0.375 mmol) (Acros Organics, Thermo Fisher Scientific, Morris Plains N.J.) in 2-methoxyethanol (10 mL) was refluxed for 1.5 h. The resulting mixture was concentrated in vacuo, and the residue was purified by column chromatography (0-40% EtOAc/hexanes) to give 50 mg of the title compound. MS: (−) m/z 522.25 (M−1).

Workup

  1. temperaturewas refluxed for 1.5 h
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. customthe residue was purified by column chromatography (0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5f550661d32d44f49877795859d330bb
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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