Ethyl orthoformate → HCID 67255018, compound

HRID 1509140Notes

Reaction equation

HRID 1509140 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:19]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:20][C:21]4[NH:26][C:25](=[N:27][NH2:28])[CH2:24][O:23][C:22]=4[N:29]=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:19]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[CH:20][C:21]4[N:26]5[CH:37]=[N:28][N:27]=[C:25]5[CH2:24][O:23][C:22]=4[N:29]=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 178452594HCID 178452594, compound

Product 1

HCID 67255018HCID 67255018, compoundYield 15%

Procedure

A solution of tert-butyl(1-(4-(2-hydrazono-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (20 mg, 0.04 mmol) in triethyl orthoformate (1 mL) was heated at 150° C. for 10 min under microwave irradiation. The reaction mixture was concentrated to dryness under reduced pressure. The resulting residue was purified by silica gel chromatography (gradient 0 to 2% MeOH in dichloromethane) to give the title compound (3 mg, 15%). 1H NMR (500 MHz, CDCl3): 8.68 (1H, s), 7.75 (1H, s), 7.34-7.26 (7H, m), 7.22-7.20 (2H,m), 5.70 (2H, s), 5.02 (1H, br s), 2.55-2.25 (4H, m), 2.10-2.03 (1H, m), 1.86-1.78 (1H, m), 1.44-1.15 (9H, br).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. customThe resulting residue was purified by silica gel chromatography (gradient 0 to 2% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-27f0c88d79f84e64a89a48f148501ffa
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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