Nitrogen → HCID 67305720, compound

HRID 876825Notes

Reaction equation

HRID 876825 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][CH:10]=[N:11]O)[CH:4]=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.N#N.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]2[N:11]=[CH:10][N:9]=[C:5]2[CH:4]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 178526359HCID 178526359, compound

Product 1

HCID 67305720HCID 67305720, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-(chloromethyl)pyridin-2-yl)-N′-hydroxyformimidamide (4-2) (820 mg, 4.4 mmol) in anhydrous THF (5 mL) cooled to 0° C. was added TFAA (1.1 g, 5.28 mmol) dropwise under N2. The reaction mixture was stirred at room temperature for 3 h. Then the mixture was treated with aqueous NaHCO3 to pH 8, concentrated and purified by chromatography on silica gel to afford the title compound (400 mg). MS (m/z): 168 (M+1)+.

Workup

  1. concentrationconcentrated
  2. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-b11b303c51a845b5a1ea4717b261aba6
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

Loading…