Hydrochloric Acid → HCID 135554955, compound

HRID 1379024Notes

Reaction equation

HRID 1379024 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[N:12]=[N:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].Cl>CO>[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

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 22909019HCID 22909019, compound

Product 1

HCID 135554955HCID 135554955, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 7-(4-fluorophenyl)-8-(pyridin-4-yl)pyrazolo[5,1-c][1,2,4]triazine (2.2 g) in methanol (20 ml) was added sodium cyanoborohydride (480 mg). The pH of the mixture was maintained at 3 to 4 for 2 hours with 1N hydrochloric acid. The procedure was repeated three additional times to completely finish the reduction. Then, the mixture was concentrated in vacuo and the residue was dissolved in 2N hydrochloric acid. The mixture was stirred at 80° C. for 30 minutes and cooled. The solution was neutralized with an aqueous saturated sodium bicarbonate solution. The separated solid was collected, washed with water and methanol and dried to give 7-(4-fluorophenyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (2.06 g).

Workup

  1. concentrationThen, the mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in 2N hydrochloric acid
  3. temperaturecooled
  4. customThe separated solid was collected
  5. washwashed with water and methanol
  6. customdried

Sources & evidence

ORD record
ord-f2d638b3eeef4d48b17ef22c64f2366c
Source dataset
uspto-grants-1997_09
Patent number
US05670503

Reaction notes

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