Diisopropylethylamine → HCID 178427630, compound

HRID 440360Notes

Reaction equation

HRID 440360 reaction equation
CN([CH2:4][CH2:5][NH:6][NH2:7])C.F[C:9]1[C:22]2C(=O)[C:20]3[CH:19]=[N:18][CH:17]=C[C:15]=3[C:14](=[O:24])[C:13]=2[C:12]([O:25][S:26]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])=[CH:11][CH:10]=1.ClC1C2C(=O)C3C=NC=CC=3C(=O)C=2C(OS(C2C=CC(C)=CC=2)(=O)=O)=CC=1.C(N(CC)C(C)C)(C)C>C1COCC1.O>[C:32]1([CH3:35])[CH:31]=[CH:30][C:29]([S:26]([O:25][C:12]2[CH:11]=[CH:10][C:9]3[NH:7][N:6]=[C:5]4[C:4]5[CH:17]=[N:18][CH:19]=[CH:20][C:15]=5[C:14](=[O:24])[C:13]=2[C:22]=34)(=[O:28])=[O:27])=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1205522-Hydrazinyl-N,N-dimethylethanamineHCID 105728809-Fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dioneHCID 199747549-Chloro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione

Product 1

HCID 178427630HCID 178427630, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere a solution of 2-(dimethylaminoethyl)hydrazine (J. Med. Chem. 7, 493, 1964) (1.86 g) in anhydrous THF (6.0 mL) is added during 30' to the stirred 9:1 mixture of 9-fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione and 9-chloro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione of Preparative Example 10b (2.4 g) in THF (24 mL) containing N,N-diisopropylethylamine (1.10 mL). A slightly exothermic reaction ensues, and the reaction temperature increases from 20° C. to 25° C. After one hour at room temperature the reaction mixture is poured in water (240 mL) and the suspension obtained is stirred for 30'. The solid is separated by suction, washed with water and dried at 40° C. to give 2-[2-(dimethylamino)ethyl)]-5-(p-toluenesulfonyloxy)isoquino[8,7,6-cd]indazole-6(2H)-one (1.44 g).

Workup

  1. customA slightly exothermic reaction
  2. temperaturethe reaction temperature increases from 20° C. to 25° C
  3. customthe suspension obtained
  4. stirringis stirred for 30'
  5. customThe solid is separated by suction
  6. washwashed with water
  7. customdried at 40° C.

Sources & evidence

ORD record
ord-127deb16558d4906b4e0c73267926d33
Source dataset
uspto-grants-1996_05
Patent number
US05519029

Reaction notes

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