HCID 19737189, compound → HCID 178506244, compound

HRID 258256Notes

Reaction equation

HRID 258256 reaction equation
[Cl:1][C:2]1[C:3]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([NH2:22])=[C:18]([NH2:21])[CH:19]=3)[CH:14]=[N:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[N:23]([O-])=O.[Na+]>C(O)(=O)C.O>[Cl:1][C:2]1[C:3]([N:12]2[C:20]3[C:15]([CH:16]=[C:17]4[N:22]=[N:23][N:21]=[C:18]4[CH:19]=3)=[CH:14][NH:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

5

Reactant 2

HCID 19737189HCID 19737189, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178506244HCID 178506244, compoundYield 113.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of 1-(3-chloro-5-trifluoromethylpyridin-2-yl)-5,6-diaminoindazole [Compound No. 81] (5.0 g) in acetic acid (20 g), a solution of sodium nitrite (0.9 g) in water (3 ml) was added dropwise at room temperature. After completion of the reaction, the reaction mixture was poured into water, and the precipitated crystals were collected by filtration, washed and dried. The crystals were purified by silica gel column chromatography with hexane-ethyl acetate (4:1) to give 5-(3-chloro-5-trifluoromethylpyridin-2-yl)[1,2,3]triazolo[4,5-f]indazole (5.0 g).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed
  4. customdried
  5. customThe crystals were purified by silica gel column chromatography with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-b34c0c77ddb74c7eb104f13441b0f5e8
Source dataset
uspto-grants-1993_11
Patent number
US05266556

Reaction notes

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