Triethylamine → 3-(2,3-Dimethyl-benzylamino)-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione

HRID 1956720Notes

Reaction equation

HRID 1956720 reaction equation
C(O[C:6]1[C:7](=[O:17])[C:8](=[O:16])[C:9]=1[NH:10][C:11]([CH3:15])([CH3:14])[CH2:12][CH3:13])CCC.Cl.[CH3:19][C:20]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][NH2:23].C(N(CC)CC)C>O1CCCC1>[CH3:19][C:20]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][NH:23][C:6]1[C:7](=[O:17])[C:8](=[O:16])[C:9]=1[NH:10][C:11]([CH3:14])([CH3:15])[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 158388373-Butoxy-4-(1,1-dimethylpropylamino)-cyclobut-3-ene-1,2-dioneHCID 178192982,3-Dimethylbenzylamine hydrochloride

Product 1

HCID 186636503-(2,3-Dimethyl-benzylamino)-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (15 mL), 3-butoxy-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione (1,20 g, 5 mmol), 2,3-dimethylbenzylamine hydrochloride (0.858 g, 5 mmol, prepared according to the procedure of R. Fuller et al., J. Med. Chem., 16 (2), 101 (1973)) and triethylamine (0.506 g, 5 mmol) were refluxed 22.5 hours and then processed in a manner similar to that of Example 4, Step 3, to provide 1.337 g of crude product. Recrystallization (twice) of this material from methanol afforded 0.777 g of the title compound as a white solid: mp 196°-198° C. MS (m/z) 300 (M+).

Workup

  1. customto provide 1.337 g of crude product
  2. customRecrystallization (twice) of this material from methanol

Sources & evidence

ORD record
ord-df8c5edf7f2d47ed827f202b58f1f93e
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

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