Triethylamine → 2-butyrylamino-5-[4,5-dihydropyridazin-3(2H)-on-6-yl]indane

HRID 1077422Notes

Reaction equation

HRID 1077422 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]3[CH2:18][CH2:19][C:20](=[O:23])[NH:21][N:22]=3)[CH:14]=2)[CH2:9]1.C(N(CC)CC)C>O1CCCC1.CN1CCN(C)C1=O>[C:1]([NH:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]3[CH2:18][CH2:19][C:20](=[O:23])[NH:21][N:22]=3)[CH:14]=2)[CH2:9]1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 140714996-(2-amino-indan-5-yl)-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 199728362-butyrylamino-5-[4,5-dihydropyridazin-3(2H)-on-6-yl]indaneYield 78.8%

Reagents, catalysts & solvents 2

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

Procedure

Butyryl chloride (4.09 g) dissolved in 20 ml of tetrahydrofuran was added dropwise to 7.26 g of 2-amino-5-[4,5-dihydropyridazin-3(2H)-on-6-yl]indane and 7.05 g of triethylamine suspended in 70 ml of 1,3-dimethyl-2-imidazolidinone. The mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into ice water, and crystals precipitated were collected by filtration, washed with water and dried. The crystals were recrystallized from ethyl acetate to obtain 7.47 g of 2-butyrylamino-5-[4,5-dihydropyridazin-3(2H)-on-6-yl]indane.

Workup

  1. customprecipitated
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4446ce5dd02640f8946fc70d42ae2bd6
Source dataset
uspto-grants-1996_08
Patent number
US05543409

Reaction notes

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