(S)-Benzyl 4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate → HCID 90102798, compound

HRID 1052583Notes

Reaction equation

HRID 1052583 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]([C@@H:18]([NH:20][C:21]1[C:22]3[C:29]([C:30]([O:32]CC4C=CC=CC=4)=[O:31])=[CH:28][NH:27][C:23]=3[N:24]=[CH:25][N:26]=1)[CH3:19])=[N:6]2>CO.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:7]([C@@H:18]([NH:20][C:21]1[C:22]3[C:29]([C:30]([OH:32])=[O:31])=[CH:28][NH:27][C:23]=3[N:24]=[CH:25][N:26]=1)[CH3:19])=[N:6]2

Participants

4

Reactant 1

HCID 73775928(S)-Benzyl 4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Product 1

HCID 90102798HCID 90102798, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

(S)-Benzyl 4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (560 mg, 1.08 mmol) was dissolved in methanol (200 ml) and hydrogenated in a Parr apparatus at 25 psi in the presence of Pd/C 10%. Once the reaction was completed, the mixture was filtered and the solvent evaporated under reduced pressure to yield 376 mg (79% yield) of the final compound, which was used in the next synthetic step without further purification.

Workup

  1. filtrationthe mixture was filtered
  2. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-4078c8f8fda848b39cdcbe0e6842ad10
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…