(S)-tert-Butyl (3-(benzyloxy)-1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate → (S)-tert-Butyl (3-hydroxy-1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate

HRID 1052369Notes

Reaction equation

HRID 1052369 reaction equation
C([O:8][CH2:9][CH2:10][C@H:11]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:12]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16](=[O:24])[C:15]2=[CH:25][CH:26]=[CH:27][N:14]2[N:13]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][CH2:9][CH2:10][C@H:11]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[C:12]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16](=[O:24])[C:15]2=[CH:25][CH:26]=[CH:27][N:14]2[N:13]=1

Participants

4

Reactant 1

HCID 131736116(S)-tert-Butyl (3-(benzyloxy)-1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate

Product 1

HCID 131736117(S)-tert-Butyl (3-hydroxy-1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-tert-Butyl (3-(benzyloxy)-1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate (0.65 g, 1.37 mmol) was dissolved in 33 mL methanol. Palladium on carbon (10%, 0.65 g, 6.11 mmol) was added and the mixture was hydrogenated at 30 psi overnight. The crude was filtered through a plug of Celite, washing several times with ethyl acetate. The combined filtrates were evaporated to give 0.52 g (99% yield) of the title compound as a white solid. Purity 100%.

Workup

  1. customwas hydrogenated at 30 psi overnight
  2. filtrationThe crude was filtered through a plug of Celite
  3. washwashing several times with ethyl acetate
  4. customThe combined filtrates were evaporated

Sources & evidence

ORD record
ord-f48cfd225ba2448297b85d1a36e14b51
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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