Ammonia → 3-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,4-triazine-5,6-diamine

HRID 2278853Notes

Reaction equation

HRID 2278853 reaction equation
[NH2:1][C:2]1[N:7]=[N:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[N:9]=2)=[N:4][C:3]=1O.[NH3:26]>S(Cl)(Cl)=O.C(#N)C>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][N:10]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:16]2[C:8]([C:5]2[N:6]=[N:7][C:2]([NH2:1])=[C:3]([NH2:26])[N:4]=2)=[N:9]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 178509143HCID 178509143, compound

Product 1

HCID 716216963-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,4-triazine-5,6-diamine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 24386Thionyl ChlorideSolvent

Procedure

3.602 g (10.677 mmol) of 6-amino-3-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,4-triazin-5-ol in 45 ml of thionyl chloride were added and heated under reflux for 3 h. The reaction mixture was diluted with 200 ml of dry acetonitrile and, with ice-cooling, added dropwise to 500 ml of concentrated aqueous ammonia solution (35% strength). The mixture was stirred at RT overnight. The acetonitrile was removed on a rotary evaporator and the precipitate was filtered off with suction. This gave 3.541 g (purity 67%, 66% of theory) of the target compound. A small amount was purified by preparative HPLC (mobile phase: acetonitrile/water with 0.1% TFA, gradient 30:70→95:5).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 h
  3. temperaturecooling
  4. customThe acetonitrile was removed on a rotary evaporator
  5. filtrationthe precipitate was filtered off with suction
  6. customA small amount was purified by preparative HPLC (mobile phase: acetonitrile/water with 0.1% TFA, gradient 30:70→95:5)

Sources & evidence

ORD record
ord-8df2702f5b31492b9ac1b557f5b50aaa
Source dataset
uspto-grants-2015_09
Patent number
US09133191B2

Reaction notes

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