Nitrogen → 2-[4-(1,1-Difluoro-ethyl)-oxazol-2-ylmethyl]-2H-[1,2,3]triazol-4-ylamine

HRID 2040042Notes

Reaction equation

N#N.[F:3][C:4]([C:7]1[N:8]=[C:9]([CH2:12][N:13]2[N:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[N:14]2)[O:10][CH:11]=1)([F:6])[CH3:5].[NH4+].[Cl-]>CCO.O.[Fe]>[F:3][C:4]([C:7]1[N:8]=[C:9]([CH2:12][N:13]2[N:17]=[C:16]([NH2:18])[CH:15]=[N:14]2)[O:10][CH:11]=1)([F:6])[CH3:5]

Participants

Conditions

Temperature: 70 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 2-[4-(1,1-difluoro-ethyl)-oxazol-2-ylmethyl]-4-nitro-2H-[1,2,3]triazole (130 mg, 0.50 mmol), iron powder (85 mg, 1.41 mmol) and NH4Cl (136 mg, 2.51 mmol) in a mixture of EtOH (2.0 mL) and water (1.0 mL) was stirred at 70° C. for 60 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (10 mL) was added followed by water (10 mL). The aq. layer was extracted with CH2Cl2 (2×10 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 05c: tR=0.47 min.

Workup

filtrationThe reaction mixture was filtered while hot and
concentrationconcentrated under reduced pressure
additionCH2Cl2 (10 mL) was added
extractionThe aq. layer was extracted with CH2Cl2 (2×10 mL)
dry with materialextracts were dried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure

Sources & evidence

ORD record: ord-e472e53e60f3450da07b6f07123e53e0
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580831B2

Reaction notes

Loading…