C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine → 3-{[(5-Methylfuran-2-yl)-(3-methyloxetan-3-yl)methyl]amino}-4-(2-oxo-2,3-dihydrobenzooxazol-7-ylamino)cyclobut-3-ene-1,2-dione

HRID 1528191Notes

Reaction equation

C(O[C:4]1[C:5](=[O:20])[C:6](=[O:19])[C:7]=1[NH:8][C:9]1[C:17]2[O:16][C:15](=[O:18])[NH:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)C.[CH3:21][C:22]1[O:26][C:25]([CH:27]([NH2:33])[C:28]2([CH3:32])[CH2:31][O:30][CH2:29]2)=[CH:24][CH:23]=1>CO>[CH3:21][C:22]1[O:26][C:25]([CH:27]([NH:33][C:4]2[C:5](=[O:20])[C:6](=[O:19])[C:7]=2[NH:8][C:9]2[C:17]3[O:16][C:15](=[O:18])[NH:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)[C:28]2([CH3:32])[CH2:29][O:30][CH2:31]2)=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 0.35 g (1.28 mmol, 1 eq) of 3-ethoxy-4-(2-oxo-2,3-dihydrobenzooxazol-7-ylamino)cyclobut-3-ene-1,2-dione and 0.278 g (1.53 mmol, 1.2 eq) of C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine in 6 ml of methanol was heated at 65° C. for 5 hours. The methanol was evaporated off and the residue was chromatographed on silica gel, eluted with 95/5 dichloromethane/methanol. The paste obtained was crystallized from ethyl ether, filtered and dried under vacuum at 40° C. 0.24 g of product was obtained in the form of a beige solid. Yield=46%. HPLC 96.4%, ES+ [410].

Workup

customThe methanol was evaporated off
customthe residue was chromatographed on silica gel
washeluted with 95/5 dichloromethane/methanol
customThe paste obtained
customwas crystallized from ethyl ether
filtrationfiltered
customdried under vacuum at 40° C

Sources & evidence

ORD record: ord-7649a49b2ff94b158ea93ec87ca8f660
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090596B2

Reaction notes

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