Sodium Methoxide → 2-{[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-pentanoic acid tert-butyl ester

HRID 1480951Notes

Reaction equation

HRID 1480951 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].Cl.[C:26]([O:30][C:31](=[O:38])[CH:32]([CH2:36][NH2:37])[CH2:33][CH2:34][CH3:35])([CH3:29])([CH3:28])[CH3:27].C[O-].[Na+]>CO>[C:26]([O:30][C:31](=[O:38])[CH:32]([CH2:36][NH:37][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])[CH2:33][CH2:34][CH3:35])([CH3:27])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylateHCID 89813040Tert-butyl 2-(aminomethyl)pentanoate hydrochloride

Product 1

HCID 898131862-{[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-pentanoic acid tert-butyl esterYield 21.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (138 mg), 2-aminomethyl-pentanoic acid tert-butyl ester HCl salt (96 mg) and NaOMe in MeOH (0.85 mL, 0.5 M solution) in MeOH (1 mL) was microwaved at 150° C. for 2 h. The mixture was cooled, concentrated with HOAc (0.1 mL), the residue was directly column purified to give the desired product (44 mg). LC MS ESI+: 476 (M+1)+.

Workup

  1. customwas microwaved at 150° C. for 2 h
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated with HOAc (0.1 mL)
  4. custompurified

Sources & evidence

ORD record
ord-b37bfb7eea9642e8b42fe581ac420405
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

Loading…