Nitrogen → 2-[2-(2-Methyl-[1,3]dioxolan-2-yl)-thiazol-5-ylmethyl]-4-nitro-2H-[1,2,3]triazole

HRID 42825Notes

Reaction equation

N#N.Cl[CH2:4][C:5]1[S:9][C:8]([C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)=[N:7][CH:6]=1.[N+:16]([C:19]1[CH:23]=[N:22][NH:21][N:20]=1)([O-:18])=[O:17].CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.O>[CH3:15][C:10]1([C:8]2[S:9][C:5]([CH2:4][N:21]3[N:20]=[C:19]([N+:16]([O-:18])=[O:17])[CH:23]=[N:22]3)=[CH:6][N:7]=2)[O:14][CH2:13][CH2:12][O:11]1

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 5-chloromethyl-2-(2-methyl-[1,3]dioxolan-2-yl)-thiazole (339 mg, 1.54 mmol) in DMF (2.0 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (160 mg, 1.40 mmol) in DMF (2.0 mL) pre-treated for 30 min with DIPEA (0.48 mL, 2.81 mmol) and the reaction mixture was stirred for 72 h at 50° C. Water (10 mL), followed by EA (10 mL) were added. The aq. layer was extracted with EA (10 mL) and the combined org. extracts were dried over NaSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (5:1 to 2:1 hept-EA) gave the title compound as a pale yellow oil: TLC:rf (1:2 hept-EA)=0.39. LC-MS-conditions 02: tR=0.89 min; [M+H]+=298.13.

Workup

additionwere added
extractionThe aq. layer was extracted with EA (10 mL)
dry with materialextracts were dried over NaSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (5:1 to 2:1 hept-EA)

Sources & evidence

ORD record: ord-cd20c6c970874ce2b37318833962e4aa
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536209B2

Reaction notes

Loading…