Hydrochloric Acid → HCID 178505616, compound

HRID 230165Notes

Reaction equation

HRID 230165 reaction equation
[NH2:1][NH2:2].COC(=O)[CH:6]([C:14]1[CH:19]=[N:18][C:17]([C:20](=O)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])=[C:16](Cl)[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13].[OH-].[Li+].Cl>C1COCC1.O>[Cl:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:20]1[C:17]2[C:16](=[N:15][C:14]([CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[F:13])=[CH:19][N:18]=2)[NH:2][N:1]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 9321HydrazineHCID 59834346[6-Chloro-5-(2-chloro-benzoyl)-pyrazin-2-yl]-(2-fluoro-phenyl)-acetic acid methyl ester

Product 1

HCID 178505616HCID 178505616, compoundYield 31.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Hydrazine (54 mg, 1.7 mmol) was added to a solution of [6-Chloro-5-(2-chloro-benzoyl)-pyrazin-2-yl]-(2-fluoro-phenyl)-acetic acid methyl ester (0.59 g, 1.4 mmol) in 50 mL THF at 0° C., and the reaction mixture was stirred and allowed to warm to room temperature. Lithium hydroxide (27 mg, 5.0 mmol) was added, and the reaction mixture was stirred for 64 hours at room temperature. Concentrated aqueous HCl (1 ml) was then added, and the reaction mixture was stirred for one hour at room temperature. The reaction mixture was poured into water, extracted with diethyl ether, and the combined organic phases were dried over MgSO4, filtered, and evaporated under reduced pressure. The residue was purified via chromatography using 5% ethyl acetate in hexanes as the eluent to afford 0.151 g of 3-(2-Chloro-phenyl)-6-(2-fluoro-benzyl)-1H-pyrazolo[3,4-b]pyrazine. Mass Spec. M+H=340.

Workup

  1. stirringthe reaction mixture was stirred for 64 hours at room temperature
  2. stirringthe reaction mixture was stirred for one hour at room temperature
  3. extractionextracted with diethyl ether
  4. dry with materialthe combined organic phases were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified via chromatography

Sources & evidence

ORD record
ord-3e7ea16521274963b7c6b5e33c032aba
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

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