Nitrogen → 4-(2-Methoxypropan-2-yl)-2-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)oxazole

HRID 82835Notes

Reaction equation

N#N.Cl[CH2:4][C:5]1[O:6][CH:7]=[C:8]([C:10]([O:13][CH3:14])([CH3:12])[CH3:11])[N:9]=1.[N+:15]([C:18]1[CH:22]=[N:21][NH:20][N:19]=1)([O-:17])=[O:16].CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.O>[CH3:14][O:13][C:10]([C:8]1[N:9]=[C:5]([CH2:4][N:20]2[N:19]=[C:18]([N+:15]([O-:17])=[O:16])[CH:22]=[N:21]2)[O:6][CH:7]=1)([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 50 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(chloromethyl)-4-(2-methoxypropan-2-yl)oxazole (134 mg, 0.71 mmol) in DMF (2.0 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (T. E. Eagles et al. Organic preparations and procedures 2 (2), 117-119, 1970; P. N. Neuman J. Heterocycl. Chem. 8, 51-56, 1971) (1.01 g of a 8% solution in DMF, 0.71 mmol) in DMF (2.0 mL) pre-treated for 30 min with DIPEA (0.24 mL, 1.41 mmol) and the reaction mixture was stirred overnight at 50° C. Water (16 mL), followed by EA (16 mL) was added. The layers were separated and the org. layer was washed with water (3×6 mL), dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (1:1 hept-EA) gave the title compound as a yellow oil: TLC: rf (1:1 hept-EA)=0.33. LC-MS-conditions 06: tR=0.69 min, [M+H]+=268.13.

Workup

additionwas added
customThe layers were separated
washlayer was washed with water (3×6 mL)
dry with materialdried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (1:1 hept-EA)

Sources & evidence

ORD record: ord-b2cbcf9e4593466cb04c723e0c46a808
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846733B2

Reaction notes

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