Cumylamine → 3-(2-Nitro-benzoylamino)-1H-furo[3,2-c]pyrazole-5-carboxylic acid (1-methyl-1-phenyl-ethyl)-amide

HRID 1642335Notes

Reaction equation

HRID 1642335 reaction equation
NC1C=CC=CC=1[C:4]([NH:6][C:7]1[NH:11][N:10]=[C:9]2[CH:12]=[C:13]([C:15](O)=[O:16])[O:14][C:8]=12)=[O:5].C(N(C(C)C)CC)(C)C.[C:31]([NH2:40])([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH3:33])[CH3:32].F[B-](F)(F)F.[N:46]1([O:55]C(N(C)C)=[N+](C)C)[C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=2N=N1.C(=O)(O)[O-:64].[Na+]>CN(C)C=O>[CH3:32][C:31]([NH:40][C:15]([C:13]1[O:14][C:8]2[C:7]([NH:6][C:4](=[O:5])[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=3[N+:46]([O-:55])=[O:64])=[N:11][NH:10][C:9]=2[CH:12]=1)=[O:16])([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:33]

Participants

7

Reactant 5

HCID 68509CumylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178507499HCID 178507499, compound

Product 1

HCID 578786433-(2-Nitro-benzoylamino)-1H-furo[3,2-c]pyrazole-5-carboxylic acid (1-methyl-1-phenyl-ethyl)-amideYield 24.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(2-Amino-benzoylamino)-furo[3,2-c]pyrazole-5-carboxylic acid (11.6 g, 0.03668 mol) was dissolved in anhydrous dimethyl formamide (DMF, 70 mL). Diisopropylethylamine (DIEA, 31.4 mL, 0.1834 mol), cumylamine (7.43 mL, 0.055 mol) and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU, 15.31 g, 0.0476 mol) were added respectively added. The solution was stirred at room temperature overnight. Then it was poured in a saturated solution of sodium bicarbonate (700 mL) and extracted with dichloromethane (2×250 ml). The organic layer was washed with water and dried over Na2SO4. The solution was then evaporated to dryness, taken up with toluene and evaporated to dryness, taken up with ethyl ether and filtered off. The solid was then purified by flash column chromatography on silica gel eluting with dichloromethane-methanol 46/4. The title compound was so obtained (3.87 g, 24.4% yield).

Workup

  1. additionadded
  2. extractionextracted with dichloromethane (2×250 ml)
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. customThe solution was then evaporated to dryness
  6. customevaporated to dryness
  7. filtrationfiltered off
  8. customThe solid was then purified by flash column chromatography on silica gel eluting with dichloromethane-methanol 46/4

Sources & evidence

ORD record
ord-626cf8f41fc6466cab3729b2fef5caef
Source dataset
uspto-grants-2012_02
Patent number
US08119641B2

Reaction notes

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