Acetic Acid → HCID 86715169, compound

HRID 1529163Notes

Reaction equation

HRID 1529163 reaction equation
[Na].[CH:2]1([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[C:15]([F:17])[CH:16]=[C:11]3[C:10]([C:18]#[N:19])=[N:9]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.[C:20]([OH:23])(=[O:22])[CH3:21].[Cl-].[NH4+:25]>CO>[C:20]([OH:23])(=[O:22])[CH3:21].[CH:2]1([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[C:15]([F:17])[CH:16]=[C:11]3[C:10]([C:18](=[NH:25])[NH2:19])=[N:9]2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 70983946HCID 70983946, compound

Product 1

HCID 86715169HCID 86715169, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under an atmosphere of argon, 296 mg (12.861 mmol) of sodium were, a little at a time, stirred into methanol. After the sodium had been consumed, 3.670 g (purity 86%, about 12.861 mmol) of 1-(cyclopentylmethyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile were added a little at a time, and the mixture was stirred at RT for 2 h. 3.004 g (50.021 mmol) of acetic acid and 825 mg (15.433 mmol) of ammonium chloride were then added, and the mixture was boiled under reflux overnight. The reaction mixture was concentrated, the residue was triturated with 1N sodium hydroxide solution and the precipitate was filtered off with suction and dried under high vacuum. This gave 2.840 g (purity 98%, 83% of theory) of the target compound.

Workup

  1. customAfter the sodium had been consumed
  2. temperatureunder reflux overnight
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was triturated with 1N sodium hydroxide solution
  5. filtrationthe precipitate was filtered off with suction
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-8f4fb29b770d48b9a2bb57c4930e8366
Source dataset
uspto-grants-2015_07
Patent number
US09090610B2

Reaction notes

Loading…