Hydrazine hydrate (1:1) → HCID 23442298, compound

HRID 2119639Notes

Reaction equation

HRID 2119639 reaction equation
[CH3:1][N:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[C:10]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[N:23]4C(=O)C5C(=CC=CC=5)C4=O)[CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH:4]=[N:3]1.O.NN>C(O)C>[NH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][C:10]1[CH:9]=[CH:8][C:7]2[NH:6][C:5]3[CH:4]=[N:3][N:2]([CH3:1])[C:14]=3[C:13](=[O:15])[C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 23442324HCID 23442324, compound

Product 1

HCID 23442298HCID 23442298, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-{2-[(1-methyl-9-oxo-4,9-dihydro-1H-pyrazolo[4,3-b]quinolin-7-yl)methyl]phenyl}-1H-isoindole-1,3(2H)-dione (EXAMPLE 25, step 2, 242 mg, 0.558 mmol) and hydrazine hydrate (0.14 ml, 2.8 mmol) in ethanol (10 ml) was refluxed for 18 h. After cooling to room temperature, the mixture was evaporated in vacuo. The obtained residue was chromatographed on a column of silica gel eluting with methanol/dichloromethane (1:20) to give 139 mg (82%) of 7-(2-aminobenzyl)-1-methyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one. 80 mg of this compound was treated with methanolic hydrochloric acid and the mixture was evaporated to give a yellow solid. This was washed with diisopropyl ether to give 78 mg of the title compound as a yellow solid.

Workup

  1. temperaturewas refluxed for 18 h
  2. customthe mixture was evaporated in vacuo
  3. customThe obtained residue was chromatographed on a column of silica gel eluting with methanol/dichloromethane (1:20)

Sources & evidence

ORD record
ord-4d68e0c87e8f4a02929f1a879f9ee6fa
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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