تفاعل #169917

معادلة التفاعل

sodium cyanoborohydride

N-{4-[4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}-1H-tetrazole-5-carboxamide

phosphorus pentachloride

→

desired product

المردود 19.0%

N-(3-Bromo-4-fluorophenyl)-N′-hydroxy-4-[(1H-tetrazol-5-ylmethyl)amino]-1,2,5-oxadiazole-3-carboximidamide

المردود 19.0%

المذيبات

pyridine

ظروف التفاعل

المعالجة

1. 1
   تركيزconcentrated
2. 2
   workup.ADDITIONrediluted with toluene
3. 3
   تركيزconcentrated to a residue
4. 4
   workup.ADDITIONThis material was diluted with ethanol (1 mL)
5. 5
   workup.STIRRINGstirred for 2 h
6. 6
   تركيزThe reaction mixture was concentrated
7. 7
   workup.ADDITIONdiluted with ethanol (1 mL)
8. 8
   workup.ADDITIONtreated with 2.0 M sodium hydroxide in water (0.2 mL)
9. 9
   workup.STIRRINGstirred for 45 min
10. 10
    أخرىPurification of the crude
11. 11
    أخرىreaction mixture by preparative LCMS

الإجراء التجريبي

A solution of N-{4-[4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}-1H-tetrazole-5-carboxamide (12 mg, 27 μmol) in pyridine (0.3 mL) was treated with phosphorus pentachloride (13 mg, 60 μmol) at 25° C. The reaction mixture was stirred at 0° C. for 2 h, concentrated, rediluted with toluene and concentrated to a residue. This material was diluted with ethanol (1 mL), treated with sodium cyanoborohydride (5 mg, 82 μmol), and stirred for 2 h. The reaction mixture was concentrated, diluted with ethanol (1 mL), treated with 2.0 M sodium hydroxide in water (0.2 mL), and stirred for 45 min. Purification of the crude reaction mixture by preparative LCMS gave the desired product (2 mg, 19%). LCMS for C11H10BrFN9O2 (M+H)+: m/z=398.0, 400.0.

المصدر