Triethylamine → 3-ethoxy-4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl)amino}-3-cyclobutene-1,2-dione

HRID 459656Notes

Reaction equation

HRID 459656 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([NH2:27])[CH:4]=[N:3]1.C(N(CC)CC)C.[CH3:35][CH2:36][O:37][C:38]1[C:42](=O)[C:40](=[O:41])[C:39]=1[O:44]CC.C(OCC)(=O)C>C(O)C.CCCCCC>[CH2:36]([O:37][C:38]1[C:39](=[O:44])[C:40](=[O:41])[C:42]=1[NH:27][C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[NH:7][C:8]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:35]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 123228Diethyl squarateHCID 685167251-methyl-N5-trityl-1H-pyrazole-4,5-diamine

Product 1

HCID 219045093-ethoxy-4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl)amino}-3-cyclobutene-1,2-dione

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

To a suspension of 1-methyl-N5-trityl-1H-pyrazole-4,5-diamine 1.60 g) in ethanol (50 ml) were added triethylamine (0.627 ml) and diethyl squarate (0.858 ml), and the mixture was stirred at room temperature for 22 hours. To the reaction mixture were added ethyl acetate (200 ml) and hexane (100 ml), and the solution was washed successively with water, 5% aqueous citric acid solution and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crystalline residue was washed with diethyl ether and dried in vacuo to give 3-ethoxy-4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3-cyclobutene-1,2-dione (1.45 g) as a solid.

Workup

  1. washthe solution was washed successively with water, 5% aqueous citric acid solution and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe crystalline residue was washed with diethyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-b2a04be7d9da44ce801bfd7ee17385cb
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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