Acetone → HCID 136116401, compound

HRID 1379031Notes

Reaction equation

HRID 1379031 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:11]3[NH:12][NH:13][CH2:14][CH2:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].Cl.C(=O)(O)[O-].[Na+].[CH3:33][C:34]([CH3:36])=O>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:11]3[NH:12][N:13]([CH:34]([CH3:36])[CH3:33])[CH2:14][CH2:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 135554955HCID 135554955, compound

Product 1

HCID 136116401HCID 136116401, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

To a mixture of 7-(4-fluorophenyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (89 mg) and sodium cyanoborohydride (63 mg) in methanol (1 ml) was added acetone (0.1 ml) with ice cooling. The pH of the mixture was adjusted to 3 to 4 with 1N hydrochloric acid and the solution was stirred at 4° C. for 30 minutes. Then, the solution was neutralized with an aqueous saturated sodium bicarbonate solution and poured into cold water. The separated oil was extracted with ethyl acetate and the extract was washed with brine, dried and concentrated in vacuo. The residue was crystallized from diethyl ether to give 7-(4-fluorophenyl)-2-isopropyl-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (75 mg).

Workup

  1. extractionThe separated oil was extracted with ethyl acetate
  2. washthe extract was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-869db801996d43b79099217d2dbff4d5
Source dataset
uspto-grants-1997_09
Patent number
US05670503

Reaction notes

Loading…