Triethylamine → HCID 19972853, compound

HRID 1077432Notes

Reaction equation

HRID 1077432 reaction equation
C(P(C#N)(CC)=O)C.[NH2:9][CH2:10][CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:20]3[CH:21]=[CH:22][C:23](=[O:26])[NH:24][N:25]=3)[CH:17]=2)[CH2:12]1.Br.[CH3:28][C:29]([CH3:34])=[CH:30][C:31](O)=[O:32].C(N(CC)CC)C>CN(C)C=O>[CH3:28][C:29]([CH3:34])=[CH:30][C:31]([NH:9][CH2:10][CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:20]3[CH:21]=[CH:22][C:23](=[O:26])[NH:24][N:25]=3)[CH:17]=2)[CH2:12]1)=[O:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 109313-Methyl-2-butenoic acidHCID 13586794DiethylphosphorylcyanideHCID 214762912-aminomethyl-5-[pyridazin-3(2H)-on-6-yl]indane hydrobromide

Product 1

HCID 19972853HCID 19972853, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under ice cooling, 1.71 g of diethylphosphoryl cyanide was added to 80 ml of a suspension containing 3.06 g of 2-aminomethyl-5-[pyridazin-3(2H)-on-6-yl]indane·hydrobromide and 1.15 g of 3-methylcrotonic acid suspended in dimethylformamide, and then 20 ml of a solution containing 2.89 g of triethylamine dissolved in dimethylformamide was added dropwise to the mixture. The resulting mixture was stirred at the same temperature for 2.5 hours. The reaction mixture was poured into ice water, and crystals precipitated were collected by filtration. The crystals obtained were washed with water, dried and then recrystallized from ethyl acetate-methanol to obtain 2.45 g of 2-[(3-methylcrotonoyl)amino]methyl-5-[pyridazin-3(2H)-on-6-yl]indane.

Workup

  1. additionwas added dropwise to the mixture
  2. customprecipitated
  3. filtrationwere collected by filtration
  4. customThe crystals obtained
  5. washwere washed with water
  6. customdried
  7. customrecrystallized from ethyl acetate-methanol

Sources & evidence

ORD record
ord-b7f4d3893dfd4f0ea75f93e0a5460e55
Source dataset
uspto-grants-1996_08
Patent number
US05543409

Reaction notes

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