Nitrogen → HCID 67958709, compound

HRID 527243Notes

Reaction equation

HRID 527243 reaction equation
N#N.[C:3]([O:9][C:10]1([C:13]2[N:14]=[C:15]([CH2:18]OS(C)(=O)=O)[O:16][CH:17]=2)[CH2:12][CH2:11]1)(=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5].[N+:24]([C:27]1[CH:31]=[N:30][NH:29][N:28]=1)([O-:26])=[O:25].CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.O>[C:3]([O:9][C:10]1([C:13]2[N:14]=[C:15]([CH2:18][N:29]3[N:28]=[C:27]([N+:24]([O-:26])=[O:25])[CH:31]=[N:30]3)[O:16][CH:17]=2)[CH2:11][CH2:12]1)(=[O:8])[C:4]([CH3:5])([CH3:6])[CH3:7]

Participants

8

Reactant 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 2781504-nitro-2H-1,2,3-triazoleHCID 86698885HCID 86698885, compound

Product 1

HCID 67958709HCID 67958709, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

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 1-(2-(((methylsulfonyl)oxy)methyl)oxazol-4-yl)cyclopropyl pivalate (400 mg, 1.26 mmol) in DMF (3.0 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) (1.80 g of a 8% solution in DMF, 1.26 mmol) in DMF (3.0 mL) pre-treated for 30 min with DIPEA (0.43 mL, 2.53 mmol) and the reaction mixture was stirred overnight at 50° C. Water (20 mL), followed by EA (20 mL) were added. The layers were separated and the org. layer was washed with water (3×10 mL), dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (7:3 hept-EA) gave the title compound as a yellow oil: TLC: rf (7:3 hept-EA)=0.34. LC-MS-conditions 06: tR=0.91 min, [M+H]+=336.22.

Workup

  1. additionwere added
  2. customThe layers were separated
  3. washlayer was washed with water (3×10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (7:3 hept-EA)

Sources & evidence

ORD record
ord-8500eb84bd4646b4bc14d106c461e82b
Source dataset
uspto-grants-2016_05
Patent number
US09346793B2

Reaction notes

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