Ethyl orthoformate → HCID 123141060, compound

HRID 1509116Notes

Reaction equation

HRID 1509116 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:26][C:25]4[C:24](=[N:34][NH2:35])[NH:23][CH2:22][CH2:21][C:20]=4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH:37](OCC)(OCC)OCC>>[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:27]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[CH:26][C:25]4[C:24]5=[N:34][N:35]=[CH:37][N:23]5[CH2:22][CH2:21][C:20]=4[N:19]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 178452592HCID 178452592, compound

Product 1

HCID 123141060HCID 123141060, compoundYield 22%

Procedure

A solution of tert-butyl(1-(4-(5-hydrazono-3-phenyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)phenyl)cyclobutyl)carbamate (40 mg, 0.08 mmol) in triethyl orthoformate (1 mL) was heated at 150° C. for 1.5 h under microwave irradiation. The resulting reaction mixture was concentrated to dryness under reduced pressure and purified by preparative HPLC (method G, gradient 5 to 95% 0.1% FA/ACN in 0.1% FA/H2O) to give the title compound (9 mg, 22%). 1H NMR (500 MHz, CDCl3): 8.47 (1H, s), 8.29 (1H, s), 7.37 (2H, d), 7.31 (2H, d), 7.28-7.26 (3H, m), 7.23-7.21 (2H, m), 5.07 (1H, br s), 4.42 (2H, t), 3.50 (2H, t), 2.55-2.25 (4H, m), 2.10-2.02 (1H, m), 1.85-1.76 (1H, m), 1.45-1.20 (9H, br).

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated to dryness under reduced pressure
  3. custompurified by preparative HPLC (method G, gradient 5 to 95% 0.1% FA/ACN in 0.1% FA/H2O)

Sources & evidence

ORD record
ord-19bcf16bac684762a92e8f5112832512
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

Loading…