Glyoxal → HCID 16113824, compound

HRID 2070049Notes

Reaction equation

HRID 2070049 reaction equation
[F:1][C:2]1[CH:38]=[CH:37][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][N:27]=[C:26]5[NH:30][N:31]=[CH:32][C:25]=45)=[CH:19][CH:18]=3)=[O:15])=[CH:9][C:8]=2[C:33]([F:36])([F:35])[F:34])=[CH:4][CH:3]=1.[CH:39]([CH:41]=[O:42])=[O:40].[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:39]([OH:40])[CH:41]([OH:42])[N:16]([C:17]4[CH:18]=[CH:19][C:20]([O:23][C:24]5[CH:29]=[CH:28][N:27]=[C:26]6[NH:30][N:31]=[CH:32][C:25]=56)=[CH:21][CH:22]=4)[C:14]3=[O:15])=[CH:9][C:8]=2[C:33]([F:35])([F:36])[F:34])=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 7860GlyoxalHCID 14798Sodium HydroxideHCID 16113488HCID 16113488, compound

Product 1

HCID 16113824HCID 16113824, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

1-[4-(4-Fluorophenoxy)-3-trifluoromethyl-phenyl]-3-[4-(1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl]urea (50 mg, 0.15 mmol) was dissolved in ethanol (5 mL), and 40% glyoxal (35 μL) and a 1 N sodium hydroxide aqueous solution (30 μL) were added thereto. The resulting mixture was stirred at 70° C. for 4 hours. The reaction solution was concentrated and then purified by reverse-phase HPLC (ODS column, 0.05% TFA-containing water/acetonitrile system, 5% to 95% linear gradient) to give the target product (9 mg, 20%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. custompurified by reverse-phase HPLC (ODS column, 0.05% TFA-containing water/acetonitrile system, 5% to 95% linear gradient)

Sources & evidence

ORD record
ord-620028a85e354e8590a499a097d8b44c
Source dataset
uspto-grants-2012_10
Patent number
US08299252B2

Reaction notes

Loading…