Ammonia → 2-{5-Amino-3-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,4-triazin-6-yl}-2-fluoropropanamide

HRID 2278843Notes

Reaction equation

HRID 2278843 reaction equation
[F:1][C:2]([C:9]1[N:14]=[N:13][C:12]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])[N:16]=2)=[N:11][C:10]=1O)([CH3:8])[C:3]([O:5]CC)=O.P(Cl)(Cl)(Cl)=O.[NH3:38].C(#[N:41])C>>[NH2:38][C:10]1[N:11]=[C:12]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])[N:16]=2)[N:13]=[N:14][C:9]=1[C:2]([F:1])([CH3:8])[C:3]([NH2:41])=[O:5]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 178471754HCID 178471754, compound

Product 1

HCID 896908452-{5-Amino-3-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,4-triazin-6-yl}-2-fluoropropanamide

Procedure

250 mg (0.522 mmol) of ethyl 2-fluoro-2-{3-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-hydroxy-1,2,4-triazin-6-yl}propanoate were admixed with 3 ml of phosphoryl chloride and stirred overnight at RT. The reaction mixture was diluted with 10 ml of dry acetonitrile and, with ice-cooling, stirred into 5 ml of concentrated aqueous ammonia solution (35% strength). Stirring was continued for 2 h at RT and for 16 h at 50° C. After cooling, the precipitate was filtered off with suction and dried in vacuo. This gave 294 mg (purity 95%, quant. yield) of the target compound.

Workup

  1. temperaturecooling
  2. stirringStirring
  3. waitwas continued for 2 h at RT and for 16 h at 50° C
  4. temperatureAfter cooling
  5. filtrationthe precipitate was filtered off with suction
  6. customdried in vacuo

Sources & evidence

ORD record
ord-9cb5e449cd944e9eadb88ff10df4b01c
Source dataset
uspto-grants-2015_09
Patent number
US09133191B2

Reaction notes

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