3-((2-Ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)-2-hydroxy-N,N-dimethylbenzamide → 2-hydroxy-N,N-dimethyl-3-(2-{[(5-methylfuran-2-yl)-(tetrahydropyran-4-yl)methyl]amino}-3,4-dioxocyclobut-1-enylamino)benzamide

HRID 2271508Notes

Reaction equation

HRID 2271508 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH:7]([NH2:14])[CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([O:17][C:18]1[C:21](=[O:22])[C:20](=O)[C:19]=1[NH:24][C:25]1[C:26]([OH:36])=[C:27]([CH:33]=[CH:34][CH:35]=1)[C:28]([N:30]([CH3:32])[CH3:31])=[O:29])C>CO>[OH:36][C:26]1[C:25]([NH:24][C:19]2[C:18](=[O:17])[C:21](=[O:22])[C:20]=2[NH:14][CH:7]([C:5]2[O:6][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:35][CH:34]=[CH:33][C:27]=1[C:28]([N:30]([CH3:32])[CH3:31])=[O:29]

Participants

4

Reactant 2

HCID 118554143-((2-Ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)-2-hydroxy-N,N-dimethylbenzamideHCID 62907069(5-Methylfuran-2-yl)(tetrahydro-2H-pyran-4-yl)methanamine

Product 1

HCID 715554442-hydroxy-N,N-dimethyl-3-(2-{[(5-methylfuran-2-yl)-(tetrahydropyran-4-yl)methyl]amino}-3,4-dioxocyclobut-1-enylamino)benzamideYield 94.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

644 mg (3.3 mmol, 2 eq) of C-(5-methylfuran-2-yl)-C-(tetrahydropyran-4-yl)methylamine were added to 500 mg (1.64 mmol, 1 eq) of 3-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)-2-hydroxy-N,N-dimethylbenzamide dissolved under hot conditions in 50 ml of methanol. The reaction medium was stirred at ambient temperature for 21 hours. The methanol was evaporated off and the residue (green oil) was chromatographed on silica gel (column Analogix SF15-40 g, Spot II) eluted with dichloromethane/methanol (gradient). 700 mg of 2-hydroxy-N,N-dimethyl-3-(2-{[(5-methylfuran-2-yl)-(tetrahydropyran-4-yl)methyl]amino}-3,4-dioxocyclobut-1-enylamino)benzamide were obtained. (M.p.=137-140° C.). Yield=94%. LC/MS: 97.1% [453]

Workup

  1. customThe methanol was evaporated off
  2. customthe residue (green oil) was chromatographed on silica gel (column Analogix SF15-40 g, Spot II)
  3. washeluted with dichloromethane/methanol (gradient)

Sources & evidence

ORD record
ord-798528913a824d39bcc12d0a19f4bff2
Source dataset
uspto-grants-2015_09
Patent number
US09120772B2

Reaction notes

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