3-Aminoazetidine, 3-BOC protected → tert-Butyl (1-(5-(thiophen-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)azetidin-3-yl)carbamate

HRID 1045723Notes

Reaction equation

HRID 1045723 reaction equation
Cl[C:2]1[C:3]2[N:4]([CH:13]=[N:14][N:15]=2)[C:5]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:6][N:7]=1.[NH:16]1[CH2:19][CH:18]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:17]1>C(O)C>[S:9]1[CH:10]=[CH:11][CH:12]=[C:8]1[C:5]1[N:4]2[CH:13]=[N:14][N:15]=[C:3]2[C:2]([N:16]2[CH2:19][CH:18]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[CH2:17]2)=[N:7][CH:6]=1

Participants

4

Reactant 2

HCID 15194053-Aminoazetidine, 3-BOC protectedHCID 584469998-Chloro-5-(thiophen-2-yl)-[1,2,4]triazolo[4,3-a]pyrazine

Product 1

HCID 58446995tert-Butyl (1-(5-(thiophen-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)azetidin-3-yl)carbamateYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 50 mL round bottom flask was charged with 8-chloro-5-(thiophen-2-yl)-[1,2,4]triazolo[4,3-a]pyrazine (0.25 g, 1.1 mmol), tert-butyl azetidin-3-ylcarbamate (540 mg, 3.1 mmol) and ethanol (5 mL). The resulting solution was refluxed overnight. Work-up: the solvent was evaporated. The residue was purified by flash column chromatography on silica gel with a 1:2 EtOAc/petroleum ether and then a 1:50 methanol/dichloromethane, to afford 130 mg (33%) of the product as a white solid. MS m/z: 373 (M+H+).

Workup

  1. temperatureThe resulting solution was refluxed overnight
  2. customthe solvent was evaporated
  3. customThe residue was purified by flash column chromatography on silica gel with a 1:2 EtOAc/petroleum ether

Sources & evidence

ORD record
ord-9219fcf68122448e9949e6b32100e3c0
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

Loading…