Dimethylformamide → HCID 15293683, compound

HRID 1637987Notes

Reaction equation

HRID 1637987 reaction equation
[N:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[CH:29][C:28]=1[O:36][CH3:37].CN(C)C=O>O>[NH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([N:1]2[CH2:6][CH2:5][N:4]([CH2:23][CH2:24][CH2:25][O:26][C:27]3[CH:32]=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[CH:29][C:28]=3[O:36][CH3:37])[CH2:3][CH2:2]2)=[N:8]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 148234453-(Piperazin-1-YL)-1H-indazole

Product 1

HCID 15293683HCID 15293683, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(1-piperazinyl)-1H-indazole (4.0 g, 20 mmol), K2CO3 (3.0 g, 22 mmol), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (5.3 g, 22 mmol), a few crystals of KI, and dimethylformamide (60 ml) was stirred at 90° C. for 5 hours. The reaction was poured into water, and the aqueous mixture was extracted with ethyl acetate. The extract was washed (brine), dried (MgSO4), and the solvent was concentrated to afford a white solid, which was triturated with diethyl ether and collected to yield, 7.0 g of product. Two recrystallizations from absolute ethyl alcohol yielded 5.3 g (64%) of analytically pure 1-[4-[3-[4-(1H-indazol-3-yl)-1-piperazinyl]propoxy]-3-methoxyphenyl]ethanone, m.p.=155-157° C.

Workup

  1. extractionthe aqueous mixture was extracted with ethyl acetate
  2. washThe extract was washed (brine)
  3. dry with materialdried (MgSO4)
  4. concentrationthe solvent was concentrated
  5. customto afford a white solid, which
  6. customwas triturated with diethyl ether
  7. customcollected
  8. customto yield
  9. customTwo recrystallizations from absolute ethyl alcohol

Sources & evidence

ORD record
ord-758cd6a3b09040b88b9aa7c4a3fda8f2
Source dataset
uspto-grants-2000_03
Patent number
US06043240

Reaction notes

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