Methyl acetoacetate → HCID 178429300, compound

HRID 2217990Notes

Reaction equation

HRID 2217990 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14](=[NH:16])[NH2:15])=[N:6]1.O=[C:22]([CH3:28])[CH2:23][C:24](OC)=[O:25]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:15]=[C:24]([OH:25])[CH:23]=[C:22]([CH3:28])[N:16]=2)=[N:6]1

Participants

4

Reactant 2

HCID 7757Methyl acetoacetate2×HCID 114039861-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide

Product 1

HCID 178429300HCID 178429300, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

2.00 g (7.43 mmol) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide (example I, step 5) are dissolved together with 1.04 g (8.91 mmol) of methyl 3-oxobutanoate in 10 ml of absolute toluene under argon and stirred under reflux for 8 hours. A further 8.91 mmol of methyl 3-oxobutanoate are added, and stirring under reflux temperature is continued for 24 hours. This is followed by cooling to 0° C., removal of the precipitated solid by filtration and drying under high vacuum. 1.98 g (72% of theory) of the product are obtained.

Workup

  1. temperatureunder reflux for 8 hours
  2. stirringstirring
  3. temperatureunder reflux temperature
  4. customremoval of the precipitated solid
  5. filtrationby filtration
  6. customdrying under high vacuum
  7. custom1.98 g (72% of theory) of the product are obtained

Sources & evidence

ORD record
ord-d41de0938ddf47e5abe42d1c66eb2bc9
Source dataset
uspto-grants-2008_08
Patent number
US07410973B2

Reaction notes

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