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

HRID 1956730Notes

Reaction equation

HRID 1956730 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.[Cl:19][C:20]1[C:21]([CH3:28])=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][NH2:24].C(N(CC)CC)C>O1CCCC1>[Cl:19][C:20]1[C:21]([CH3:28])=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][NH:24][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 17819390(3-Chloro-2-methylphenyl)methanamine hydrochloride

Product 1

HCID 541468383-(3-Chloro-2-methyl-benzylamino)-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dioneYield 89.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (10 mL), 3-butoxy-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione (1,20 g, 5.0 mmol, Example 3), 3-chloro-2-methylbenzylamine hydrochloride (0.96 g, 5.0 mmol, Example 96, Step 1), and triethylamine (0.51 g, 5.0 mmol) were stirred together at room temperature for 65 hours. Processing the reaction mixture as in Example 96, Step 2 provided 1.44 g of a white solid. Two recrystallizations of the crude product from methanol gave 1.12 g of the title compound as a fluffy, white solid: mp 236°-237° C. (softens 233° C.). MS (m/z) 321/323 ([M+H]+). HPLC indicates a major component (99.6%).

Sources & evidence

ORD record
ord-1e6fa34ac1f949d69cff57b82c64d13f
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

Loading…