Water → 6'-(2-Methyl-5-(1,3,4-oxadiazol-2-yl)phenyl)spiro[cyclopentane-1,3'-indolin]-2'-one

HRID 1619156Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][C:3]=1[C:12]1[CH:20]=[C:19]2[C:15]([C:16]3([CH2:25][CH2:24][CH2:23][CH2:22]3)[C:17](=[O:21])[NH:18]2)=[CH:14][CH:13]=1.[CH3:26]OC(OC)OC.O>C(O)(=O)C>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[O:7][CH:26]=[N:9][N:8]=2)=[CH:4][C:3]=1[C:12]1[CH:20]=[C:19]2[C:15]([C:16]3([CH2:25][CH2:24][CH2:23][CH2:22]3)[C:17](=[O:21])[NH:18]2)=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A stirred mixture of 4-methyl-3-(2′-oxospiro[cyclopentane-1,3′-indoline]-6′-yl)benzohydrazide (preparation 53, 0.16 g, 0.24 mmol) and trimethylorthoformate (0.24 mL, 1.44 mmol) in acetic acid (3 mL) were heated to 150° C. in a sealed tube. After 3 hours, the mixture was cooled, poured into water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried (MgSO4) and evaporated in vacuo. Purification of the residue by flash chromatography (1:1 hexanes/ethyl acetate) gave the title compound (0.05 g, 60%) as a white solid.

Workup

temperaturethe mixture was cooled
extractionextracted with ethyl acetate
washThe organic layer was washed with water, brine
dry with materialdried (MgSO4)
customevaporated in vacuo
customPurification of the residue by flash chromatography (1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-6d337581212d468ea1c8b5354951c013
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772288B2

Reaction notes

Loading…