Ammonia → 3-[1-(Cyclopentylmethyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl]-7,7-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-e][1,2,4]triazin-6-one

HRID 1529175Notes

Reaction equation

HRID 1529175 reaction equation
P(Cl)(Cl)(Cl)=O.[CH:6]1([CH2:11][N:12]2[C:16]3=[N:17][CH:18]=[C:19]([F:21])[CH:20]=[C:15]3[C:14]([C:22]3[N:23]=[N:24][C:25]([C:29]([CH3:35])([CH3:34])[C:30]([O:32]C)=O)=[C:26](O)[N:27]=3)=[N:13]2)[CH2:10][CH2:9][CH2:8][CH2:7]1.[NH3:36]>C(#N)C>[CH:6]1([CH2:11][N:12]2[C:16]3=[N:17][CH:18]=[C:19]([F:21])[CH:20]=[C:15]3[C:14]([C:22]3[N:23]=[N:24][C:25]4[C:29]([CH3:34])([CH3:35])[C:30](=[O:32])[NH:36][C:26]=4[N:27]=3)=[N:13]2)[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178500123HCID 178500123, compound

Product 1

HCID 714691503-[1-(Cyclopentylmethyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl]-7,7-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-e][1,2,4]triazin-6-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5 ml (53.642 mmol) of phosphoryl chloride were added to 376 mg (0.863 mmol) of methyl 2-{3-[1-(cyclopentylmethyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-hydroxy-1,2,4-triazin-6-yl}-2-methylpropanoate, and the mixture was stirred at RT overnight. The reaction solution was diluted with 20 ml of dry acetonitrile and, with ice-cooling, slowly added dropwise to 83 ml of a 25% strength aqueous ammonia solution, and the mixture was stirred at RT overnight. The reaction mixture was concentrated on a rotary evaporator and the precipitate was filtered off. The residue was triturated with DMF/methanol, filtered off with suction and dried under high vacuum. This gave 84 mg of the target compound (24% of theory).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at RT overnight
  3. concentrationThe reaction mixture was concentrated on a rotary evaporator
  4. filtrationthe precipitate was filtered off
  5. customThe residue was triturated with DMF/methanol
  6. filtrationfiltered off with suction
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-f4ee6cc7e9b547a5bcf0f693c800c277
Source dataset
uspto-grants-2015_07
Patent number
US09090610B2

Reaction notes

Loading…