C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine → HCID 178425500, compound

HRID 1528186Notes

Reaction equation

HRID 1528186 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH:7]([NH2:13])[C:8]2([CH3:12])[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([NH:23][C:24]3[C:25](=O)[C:26](=[O:30])[C:27]=3[O:28]C)[C:17]=2[NH:16][N:15]=1>CO>[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([NH:23][C:24]3[C:27](=[O:28])[C:26](=[O:30])[C:25]=3[NH:13][CH:7]([C:5]3[O:6][C:2]([CH3:1])=[CH:3][CH:4]=3)[C:8]3([CH3:12])[CH2:9][O:10][CH2:11]3)[C:17]=2[NH:16][N:15]=1

Participants

4

Reactant 2

HCID 89525357C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamineHCID 178493669HCID 178493669, compound

Product 1

HCID 178425500HCID 178425500, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 263 mg (1.45 mmol, 1.2 eq) of C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine and 1.02 g (1.21 mmol, 1 eq) of 3-(3H-benzotriazol-4-ylamino)-4-methoxycyclobut-3-ene-1,2-dione at 29% in 25 ml of methanol was heated at 50° C. for 24 hours. The insoluble material (dimer) was filtered off and the filtrate was evaporated. The residue was chromatographed on silica gel (column puriFlash PF-30SIHP/40G, Spot II) eluted with dichloromethane/methanol (gradient). The solid was taken up with ethyl acetate and this organic phase was washed several times with a 1 N sodium dihydrogen phosphate solution, dried over magnesium sulfate, filtered and evaporated. 205 mg of 3-(3H-benzotriazol-4-ylamino)-4-{[(5-methyl furan-2-yl)-(3-methyloxetan-3-yl)methyl]amino}cyclobut-3-ene-1,2-dione were obtained in the form of a yellow solid. (Mp=178-180° C.). Yield=43%, LC/MS: 95.97% [393].

Workup

  1. filtrationThe insoluble material (dimer) was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed on silica gel (column puriFlash PF-30SIHP/40G, Spot II)
  4. washeluted with dichloromethane/methanol (gradient)
  5. washthis organic phase was washed several times with a 1 N sodium dihydrogen phosphate solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-0feb7e392efd40f3b32246fcfe036548
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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