Triethylamine → HCID 53993022, compound

HRID 1956728Notes

Reaction equation

HRID 1956728 reaction equation
Cl.[CH3:2][C:3]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:4]=1[CH2:5][NH2:6].C(N(CC)CC)C.C([O:23][C:24]1[C:25](=[O:35])[C:26](=O)[C:27]=1[NH:28][C:29]([CH3:33])([CH3:32])[CH2:30][CH3:31])CCC>O1CCCC1>[CH3:2][C:3]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:4]=1[CH2:5][NH:6][C:26]1[C:25](=[O:35])[C:24](=[O:23])[C:27]=1[NH:28][C:29]([CH3:32])([CH3:33])[CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 158388373-Butoxy-4-(1,1-dimethylpropylamino)-cyclobut-3-ene-1,2-dioneHCID 17819421HCID 17819421, compound

Product 1

HCID 53993022HCID 53993022, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (10 mL), 2,5-dimethylbenzylamine hydrochloride (0.858 g, 5.0 mmol, Example 94, Step 2), triethylamine (0.51 g, 5.0 mmol), and 3-butoxy-4-(1,1-dimethylpropylamino)-cyclobut-3-ene-1,2-dione (1,20 g, 5.0 mmol, Example 3) were stirred together at room temperature for approximately 18 hours. After removal of solvent the residue was triturated with water, with diethyl ether, and dried to give 1.31 g of a light yellow solid. Three recrystallizations of the crude product from acetonitrile provided 0.812 g of the title compound as a fluffy, white solid: mp 199°-200° C. (softens 195° C.). MS (m/z) 301 ([M+H]+). HPLC indicates a major component (>99%).

Workup

  1. customAfter removal of solvent the residue
  2. customwas triturated with water, with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-391ea8352e7c4f6cbb12032b9ca607f7
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

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