Hydrochloric Acid → 7-[4-[2-(DIMETHYLAMINO)ETHOXY]BENZYL]-1-METHYL-1,4-DIHYDRO-9H-PYRAZOLO[4,3-b]QUINOLIN-9-ONE HYDROCHLORIDE

HRID 2119633Notes

Reaction equation

HRID 2119633 reaction equation
CN(C)CCOC1C=CC(CC2C=CC3N=C4C=NN(C)C4=C([Cl:25])C=3C=2)=CC=1.C(C1C=CC2N=C3C=NN(C)C3=C(Cl)C=2C=1)C1C=CC=CC=1.[CH3:51][N:52]([CH3:78])[CH2:53][CH2:54][O:55][C:56]1[CH:77]=[CH:76][C:59]([CH2:60][C:61]2[CH:70]=[CH:69][C:68]3[NH:67][C:66]4[CH:71]=[N:72][N:73]([CH3:74])[C:65]=4[C:64](=[O:75])[C:63]=3[CH:62]=2)=[CH:58][CH:57]=1.Cl>>[CH3:78][N:52]([CH3:51])[CH2:53][CH2:54][O:55][C:56]1[CH:57]=[CH:58][C:59]([CH2:60][C:61]2[CH:70]=[CH:69][C:68]3[NH:67][C:66]4[CH:71]=[N:72][N:73]([CH3:74])[C:65]=4[C:64](=[O:75])[C:63]=3[CH:62]=2)=[CH:76][CH:77]=1.[ClH:25].[CH3:78][N:52]([CH3:51])[CH2:53][CH2:54][O:55][C:56]1[CH:57]=[CH:58][C:59]([CH2:60][C:61]2[CH:70]=[CH:69][C:68]3[NH:67][C:66]4[CH:71]=[N:72][N:73]([CH3:74])[C:65]=4[C:64](=[O:75])[C:63]=3[CH:62]=2)=[CH:76][CH:77]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 234423817-benzyl-9-chloro-1-methyl-1H-pyrazolo[4,3-b]quinolineHCID 234423827-[4-[2-(dimethylamino)ethoxy]benzyl]-9-chloro-1-methyl-1H-pyrazolo[4,3-b]-quinolineHCID 234424517-[4-(2-(Dimethylamino)ethoxy)benzyl]-1-methyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one

Product 2

HCID 234424517-[4-(2-(Dimethylamino)ethoxy)benzyl]-1-methyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-oneHCID 234424747-[4-[2-(DIMETHYLAMINO)ETHOXY]BENZYL]-1-METHYL-1,4-DIHYDRO-9H-PYRAZOLO[4,3-b]QUINOLIN-9-ONE HYDROCHLORIDEYield 27%

Procedure

7-[4-(2-(Dimethylamino)ethoxy)benzyl]-1-methyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one was prepared according to the procedure of step 3 in EXAMPLE 11 using 7-[4-[2-(dimethylamino)ethoxy]benzyl]-9-chloro-1-methyl-1H-pyrazolo[4,3-b]-quinoline (Example 18, step 2), instead of 7-benzyl-9-chloro-1-methyl-1H-pyrazolo[4,3-b]quinoline. 7-[4-(2-(Dimethylamino)ethoxy)benzyl]-1-methyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one (18 mg, 0.048 mmol) was treated with methanolic hydrochloric acid (5 ml) and the mixture was evaporated to give a yellow solid. The solid was recrystallized from 2-propanol and diethyl ether to afford 7 mg (27%) of the titled compound as a pale yellow solid.

Workup

  1. customthe mixture was evaporated
  2. customto give a yellow solid
  3. customThe solid was recrystallized from 2-propanol and diethyl ether

Sources & evidence

ORD record
ord-0f3a8a696e0e4e05ae53ac3432f55455
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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