Triethylamine → HCID 17819378, compound

HRID 1956729Notes

Reaction equation

HRID 1956729 reaction equation
C(O[C:6]1[C:7](=[O:16])[C:8](=[O:15])[C:9]=1[NH:10][C:11]([CH3:14])([CH3:13])[CH3:12])CCC.[CH3:17][C:18]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:19]=1[CH2:20][NH2:21].C(N(CC)CC)C>O1CCCC1>[C:11]([NH:10][C:9]1[C:8](=[O:15])[C:7](=[O:16])[C:6]=1[NH:21][CH2:20][C:19]1[CH:22]=[C:23]([CH3:26])[CH:24]=[CH:25][C:18]=1[CH3:17])([CH3:12])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66735Benzenemethanamine, 2,5-dimethyl-HCID 178193893-Butoxy-4-tert-butylamino-cyclobut-3-ene-1,2-dione

Product 1

HCID 17819378HCID 17819378, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (10 mL), 3-butoxy-4-tert-butylamino-cyclobut-3-ene-1,2-dione (1.13 g, 5.0 mmol, Example 1), 2,5-dimethylbenzylamine (0.858 g, 5.0 mmol), and triethylamine (0.51 g, 5.0 mmol) were stirred together at room temperature for approximately 18 hours. Following removal of solvent, the residue was triturated with water, with diethyl ether, and dried to give 0.698 g of a cream-colored solid. Three recrystallizations of this material from methanol afforded 0.444 g of the title compound as a white solid: mp 246°-247° C. (softens 242° C.). MS (m/z) 287 ([M+H]+). HPLC indicates a major component (>99%).

Workup

  1. customremoval of solvent
  2. customthe residue was triturated with water, with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-59d2bb164b0647abaa8d92007a506864
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

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