Trifluoroacetic acid → HCID 67110334, compound

HRID 2080680Notes

Reaction equation

HRID 2080680 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].FC(F)(F)C(O)=O.[CH3:13][C:14]1[O:18][N:17]=[C:16]([C:19]2[N:24]=[CH:23][C:22]([O:25][C:26]3[CH:31]=[CH:30][C:29]([NH:32][C:33]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)=[O:34])=[C:28]([CH2:41][N:42]4[CH2:46][CH2:45][CH2:44][C:43]4=[O:47])[CH:27]=3)=[CH:21][CH:20]=2)[N:15]=1>>[CH3:13][C:14]1[O:18][N:17]=[C:16]([C:19]2[N:24]=[CH:23][C:22]([O:25][C:26]3[CH:27]=[C:28]([CH2:41][N:42]4[CH2:46][CH2:45][CH2:44][C:43]4=[O:47])[C:29]([NH:32][C:33]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)=[O:34])=[C:30]([N+:1]([O-:4])=[O:2])[CH:31]=3)=[CH:21][CH:20]=2)[N:15]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 24434Potassium NitrateHCID 57433640HCID 57433640, compound

Product 1

HCID 67110334HCID 67110334, compoundYield 95.2%

Conditions

Temperature
80 °C

Procedure

126 mg of potassium nitrate was added to a trifluoroacetic acid (3 ml) solution of 117 mg of N-{4-{[6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]oxy}-2-[(2-oxopyrrolidin-1-yl)methyl]phenyl}pyridine-2-carboxamide, and stirred under heat at 80° C. for 7 hours. Trifluoroacetic acid was evaporated away under reduced pressure, then chloroform was added to the residue, and washed with aqueous saturated sodium hydrogencarbonate solution. The organic layer was dried, and the solvent was evaporated away under reduced pressure to obtain 122 mg of N-{4-{[6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]oxy}-2-nitro-6-[(2-oxopyrrolidin-1-yl)methyl]phenyl}pyridine-2-carboxamide as a brown oil.

Workup

  1. customTrifluoroacetic acid was evaporated away under reduced pressure
  2. additionchloroform was added to the residue
  3. washwashed with aqueous saturated sodium hydrogencarbonate solution
  4. customThe organic layer was dried
  5. customthe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-612c0a4b733a4df78c3358c71adcb89e
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

Loading…