Sodium Hydroxide → Ethyl 1-[(5-ethyl-1,3-oxazol-2-yl)methyl]-7-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylate

HRID 44576Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[N:9]([CH2:11][C:12](=[O:19])[NH:13][CH2:14][C:15](=O)[CH2:16][CH3:17])[N:8]=[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:6]=2[CH2:5][CH2:4][CH2:3]1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:16]([C:15]1[O:19][C:12]([CH2:11][N:9]2[C:10]3[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][C:6]=3[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:8]2)=[N:13][CH:14]=1)[CH3:17]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 506 mg (1.51 mmol) of ethyl 7-oxo-1-{2-oxo-2-[(2-oxobutyl)amino]ethyl}-4,5,6,7-tetrahydro-1H-indazole-3-carboxylate in toluene (45 mL) was treated with 0.422 mL (4.53 mmol) of phosphoric trichloride and heated at 90° C. for 15 hours. The mixture was cooled to room temperature, poured into ice and neutralized with NaOH 5N. The aqueous phase was extracted with dichloromethane and the organic layer afforded 425 mg of crude that was purified on silica gel (eluant hexane/ethylacetate 7/3). 285 mg of the title compound were thus isolated (60% yield).

Workup

temperatureThe mixture was cooled to room temperature
extractionThe aqueous phase was extracted with dichloromethane
customthe organic layer afforded 425 mg of crude that
customwas purified on silica gel (eluant hexane/ethylacetate 7/3)

Sources & evidence

ORD record: ord-ef58c6da9d5d49d5847539a4e9fcd687
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541429B2

Reaction notes

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