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

HRID 1619155Notes

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][C:27](C)(C)C([O-])([O-])[O-].O>C(O)(=O)C>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[O:7][C:26]([CH3:27])=[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, 0.05 g, 0.16 mmol) and trimethylorthoacetate (0.04 mL, 0.19 mmol) in acetic acid (1 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 (0.02 g, 35%) 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-6e53e0c9a30c4bab8e3deb018722a035
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772288B2

Reaction notes

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