Hydrochloric Acid → HCID 136395921, compound

HRID 1379030Notes

Reaction equation

HRID 1379030 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]2[N:10]=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:6]2[NH:5]1)(=O)[CH3:2].B.O1CCCC1.Cl>O1CCCC1>[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]2[N:10]=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:12]([C:13]3[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=3)=[C:6]2[NH:5]1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 135554938HCID 135554938, compound

Product 1

HCID 136395921HCID 136395921, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-acetyl-7-(4-fluorophenyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (59 mg) in tetrahydrofuran was added borane-tetrahydrofuran complex (1.0M solution in tetrahydrofuran, 1 ml) dropwise. The solution was stirred at ambient temperature for 5 hours and to the solution was added dropwise 1N-hydrochloric acid (3 ml). The solution was stirred at 80° C. for 20 minutes and the tetrahydrofuran was evaporated. Then, the aqueous solution was neutralized with an aqueous saturated sodium bicarbonate solution and the separated oil was extracted with dichloromethane. The extract was dried and concentrated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from ethyl acetate to give 2-ethyl-7-(4-fluorophenyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (30 ml).

Workup

  1. stirringThe solution was stirred at 80° C. for 20 minutes
  2. customthe tetrahydrofuran was evaporated
  3. extractionthe separated oil was extracted with dichloromethane
  4. customThe extract was dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel
  7. customthe obtained oil was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-75117061779c489389d7f53b586a29cd
Source dataset
uspto-grants-1997_09
Patent number
US05670503

Reaction notes

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