Ethanol → HCID 178517576, compound

HRID 2278856Notes

Reaction equation

HRID 2278856 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3](=O)[C:4](OC)=[O:5].[F:11][C:12]1[CH:31]=[CH:30][CH:29]=[CH:28][C:13]=1[CH2:14][N:15]1[C:19]2=[N:20][CH:21]=N[CH:23]=[C:18]2[C:17]([C:24](=[NH:27])[NH:25][NH2:26])=[N:16]1.[CH2:32](O)C>>[F:11][C:12]1[CH:31]=[CH:30][CH:29]=[CH:28][C:13]=1[CH2:14][N:15]1[C:19]2=[N:20][CH:21]=[CH:32][CH:23]=[C:18]2[C:17]([C:24]2[N:25]=[N:26][C:3]([C:2]([F:10])([F:9])[F:1])=[C:4]([OH:5])[N:27]=2)=[N:16]1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 2734931Methyl 3,3,3-trifluoro-2-oxopropanoateHCID 178512736HCID 178512736, compound

Product 1

HCID 178517576HCID 178517576, compound

Procedure

1.098 g (7.035 mmol) of methyl 3,3,3-trifluoro-2-oxopropanoate in 10 ml of ethanol were initially introduced and heated to reflux. Then, 2.000 g (7.035 mmol) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboximidohydrazide suspended in 25 ml of ethanol were added and the mixture was heated under reflux overnight. After cooling, the mixture was filtered, and the filtercake was washed with a little ethanol and purified by preparative HPLC (mobile phase: acetonitrile/water with 0.1% TFA, ratio 45:55). This gave 710 mg of the target compound (purity 93%; 24% of theory).

Workup

  1. temperatureheated to reflux
  2. additionwere added
  3. temperaturethe mixture was heated
  4. temperatureunder reflux overnight
  5. temperatureAfter cooling
  6. filtrationthe mixture was filtered
  7. washthe filtercake was washed with a little ethanol
  8. custompurified by preparative HPLC (mobile phase: acetonitrile/water with 0.1% TFA, ratio 45:55)

Sources & evidence

ORD record
ord-133a259007f7432b80c5352b74c9b466
Source dataset
uspto-grants-2015_09
Patent number
US09133191B2

Reaction notes

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