Pyridine → HCID 22909121, compound

HRID 1379037Notes

Reaction equation

HRID 1379037 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[C:11]3[NH:12][N:13]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:14][CH2:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:33](Cl)(=[O:35])[CH3:34].C(=O)(O)[O-].[Na+]>CN1CCCC1=O.C(OCC)(=O)C>[C:33]([N:12]1[C:11]2=[C:20]([C:21]3[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=3)[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[N:9][N:10]2[CH2:15][CH2:14][N:13]1[CH2:16][CH:17]([CH3:19])[CH3:18])(=[O:35])[CH3:34]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 136395922HCID 136395922, compound

Product 1

HCID 22909121HCID 22909121, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a mixture of 7-(4-fluorophenyl)-2-isobutyl-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (70 mg, 0.199 mmol) and pyridine (31 mg, 0.398 mmol) in N-methyl-2-pyrrolidone (1.2 ml) was added acetyl chloride (19 mg, 0.239 mmol) in N-methyl-2-pyrrolidone (0.3 ml) at ambient temperature. The reaction mixture was stirred for 1 hour, then aqueous saturated sodium bicarbonate and ethyl acetate were added thereto. The organic phase was separated, and washed with water, brine, and dried over sodium sulfate. The solvent was evaporated, and the obtained residue was purified by column chromatography on silica gel (eluent:dichloromethane/methanol; 100/1~40/1). The fractions containing the object compound were concentrated in vacuo and the obtained oil was crystallized from diisopropyl ether to give 1-acetyl-7-(4-fluorophenyl)-2-isobutyl-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo-[5,1-c][1,2,4]triazine (57.0 mg).

Workup

  1. customThe organic phase was separated
  2. washwashed with water, brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated
  5. customthe obtained residue was purified by column chromatography on silica gel (eluent:dichloromethane/methanol; 100/1~40/1)
  6. additionThe fractions containing the object compound
  7. concentrationwere concentrated in vacuo
  8. customthe obtained oil was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-b61adf3b975142ba97adf9b5daf34dda
Source dataset
uspto-grants-1997_09
Patent number
US05670503

Reaction notes

Loading…