Dimethylamine → HCID 15860292, compound

HRID 1384812Notes

Reaction equation

HRID 1384812 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[C:11]([CH2:22][C:23]([OH:25])=O)=[N:12][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:14](=[O:15])[C:3]1=2.[C:26](N1C=CN=C1)([N:28]1C=CN=[CH:29]1)=O.CNC>O1CCCC1>[CH3:26][N:28]([CH3:29])[C:23](=[O:25])[CH2:22][C:11]1[C:4]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[N:2]([CH3:1])[C:3]=2[C:14](=[O:15])[N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 21183746HCID 21183746, compound

Product 1

HCID 15860292HCID 15860292, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

A suspension of 1 g (3 mmol) of 5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetic acid and of 0.7 g (4.3 mmol) of 1,1′-carbonylbis-1H-imidazole in 200 ml of tetrahydrofuran is stirred for 2 h at 60° C. The reaction mixture is cooled to 25° C., an excess of liquefied dimethylamine in solution in tetrahydrofuran is added and the reaction mixture is stirred for 72 h at room temperature. It is concentrated under reduced pressure, 300 ml of water are added and the precipitate is collected by filtration, washed with water and with ether and recrystallized from propan-2-ol. 0.75 g (2 mmol) of solid is isolated.

Workup

  1. concentrationIt is concentrated under reduced pressure, 300 ml of water
  2. additionare added
  3. filtrationthe precipitate is collected by filtration
  4. washwashed with water and with ether
  5. customrecrystallized from propan-2-ol

Sources & evidence

ORD record
ord-cad343a3c9134ad1b6db7e0ef648bc12
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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