Potassium Carbonate → HCID 44539338, compound

HRID 455139Notes

Reaction equation

HRID 455139 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][N:11]3[C:17]=2[CH2:18][C:19]2[N:23]=[C:22]([C:24]([O:26]CC)=O)[O:21][N:20]=2)=[CH:4][CH:3]=1.[NH2:29][OH:30].Cl.C([O-])([O-])=O.[K+].[K+]>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][N:11]3[C:17]=2[CH2:18][C:19]2[N:23]=[C:22]([C:24]([NH:29][OH:30])=[O:26])[O:21][N:20]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 67028687HCID 67028687, compound

Product 1

HCID 44539338HCID 44539338, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-((2-(4-chlorophenyl)-6-fluoroimidazo[1,2-a]pyridin-3-yl)methyl)-1,2,4-oxadiazole-5-carboxylate (0.125 mmol, 50.0 mg) in EtOH (10 mL) was added NH2OH.HCl (0.75 mmol, 52.1 mg) and K2CO3 (0.375 mmol, 51.8 mg) at r.t. The reaction mixture was stirred for 30 mins at r.t., and filtered. The filtrate was concentrated under reduced pressure, to give the title product (30 mg, 60.0%), as a white solid. m/e+=388 (M+H+). 1H NMR (300 MHz, in DMSO-d6): δ 12.14 (1H, D, brd, OH), δ 9.87 (1H, D, brd, NH), δ 8.69-8.68 (1H, D, dd, J=5.2, 2.4 Hz, ArH), δ 7.81-7.79 (2H, D, d, J=8.4 Hz, ArH), δ 7.74-7.71 (1H, D, dd, J=9.6, 5.2 Hz, ArH), δ 7.55-7.53 (2H, D, d, J=8.4 Hz, ArH), δ 7.47-7.41 (1H, D, m, ArH), and δ 4.73 (2H, D, s, CH2).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-48eee2171b8f411e83a5fe2259712023
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

Loading…