Triethylamine → HCID 19972832, compound

HRID 1451785Notes

Reaction equation

HRID 1451785 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:19]3[CH2:20][CH2:21][C:22](=[O:25])[NH:23][N:24]=3)[CH:16]=2)[CH2:11]1.[C:26](Cl)(=[O:30])[CH2:27][CH2:28][CH3:29]>CN1CCN(C)C1=O.O1CCCC1>[C:26]([NH:8][CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:19]3[CH2:20][CH2:21][C:22](=[O:25])[NH:23][N:24]=3)[CH:16]=2)[CH2:11]1)(=[O:30])[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 21476304HCID 21476304, compound

Product 1

HCID 19972832HCID 19972832, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 66611,3-Dimethyl-2-imidazolidinoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (1.47 g) was added to 15 ml of a suspension containing 1.57 g of 2-aminomethyl-5-[4,5-dihydropyridazin-3(2H)-on-6-yl]indane suspended in 1,3-dimethyl-2-imidazolidinone, and the mixture was stirred at room temperature for 10 minutes. Then, 0.83 g of butyryl chloride dissolved in 8 ml of tetrahydrofuran was added dropwise to the mixture, and the resulting mixture was stirred for 1 hour. 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 1.47 g of 2-(butyrylamino)methyl-5-[4,5-dihydropyridazin-3(2H)-on-6-yl]indane.

Workup

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

Sources & evidence

ORD record
ord-2bdcc112057246acab95fa4d304f2cfc
Source dataset
uspto-grants-1997_02
Patent number
US05605901

Reaction notes

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