Cumylamine → 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(2-phenylpropan-2-yl)-1,3,4-oxadiazol-2-amine

BOP (455 mg, 1.029 mmol) was added to a stirred mixture of 5-(3-iodo-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2(3H)-one (450 mg, 0.935 mmol), 2-phenylpropan-2-amine (0.442 mL, 3.27 mmol) and diisopropylethylamine (0.33 mL, 1.87 mmol) in DMF (5.0 mL). The mixture was stirred at RT for 14 h. It was treated with BOP (300 mg) and 2-phenylpropan-2-amine (0.3 mL) and heated to 65° C. for 3 h. The mixture was diluted with water and extracted with EtOAc (50 mL). The organic layer was washed with brine, dried over MgSO4, and concentrated. Purification (eluting with 20-70% EtOAc in Hex) afforded 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(2-phenylpropan-2-yl)-1,3,4-oxadiazol-2-amine (103.6 mg, 19%) as a white amorphous solid. MS (ESI, pos. ion) m/z: 601.0 (M+1).

1. temperatureheated to 65° C. for 3 h
2. extractionextracted with EtOAc (50 mL)
3. washThe organic layer was washed with brine
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. customPurification (eluting with 20-70% EtOAc in Hex)

ORD-Eintrag

ord-34f910f7b04749589ffde63eeed175f9

Quelldatensatz

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09321756B2