6-Benzyl-1, 7-dimethyl-4-nitro-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine → 6-Benzyl-1, 7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridin-4-amine
Reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([N+:21]([O-])=O)[C:15]3[N:16]([C:17]([CH3:20])=[N:18][N:19]=3)[C:11]=2[CH:10]=[C:9]1[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.O1CCCC1.[Pd]>[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([NH2:21])[C:15]3[N:16]([C:17]([CH3:20])=[N:18][N:19]=3)[C:11]=2[CH:10]=[C:9]1[CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
A degassed suspension of 6-benzyl-1,7-dimethyl-4-nitro-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (0.20 g, 0.62 mmol, from Step 2) in methanol (20 mL) and tetrahydrofuran (20 mL) was hydrogenated over Palladium (10% on carbon (Degussa type, Aldrich), 0.066 g, 0.062 mmol) under 1 atm H2 overnight. The reaction mixture was filtered, and the solvent was removed in vacuo. The product was purified by flash chromatography, eluting with 7% MeOH/DCM (0.7% NH4OH). The product thus obtained (190 mg) was triturated in 2.5 mL MTBE and 0.25 mL DCM. The solid title product of step 3 was isolated by filtration and dried at 40° C. under vacuum overnight. Yield: (0.13 g, 69%).
Workup
- filtrationThe reaction mixture was filtered
- customthe solvent was removed in vacuo
- customThe product was purified by flash chromatography
- washeluting with 7% MeOH/DCM (0.7% NH4OH)
- customThe product thus obtained (190 mg)
- customwas triturated in 2.5 mL MTBE
Sources & evidence
- ORD record
- ord-45e6ab2c6099431ebaaf723150840cbf
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309246B2
Reaction notes
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