10-Azetidin-1-yl-3-pyridin-2-ylethynyl-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohepta[f]indene-7-carboxylic acid tert-butyl ester → 10-Azetidin-1-yl-3-(2-pyridin-2-yl-ethyl)-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohepta[f]indene-7-carboxylic acid tert-butyl ester

HRID 528720Notes

Reaction equation

HRID 528720 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:33][CH2:32][C:12]2=[C:13]([N:28]3[CH2:31][CH2:30][CH2:29]3)[N:14]3[C:18]([N:19]=[C:11]2[CH2:10][CH2:9]1)=[C:17]([C:20]#[C:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[CH:16]=[N:15]3)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[OH-].[Pd+2].[OH-]>[C:1]([O:5][C:6]([N:8]1[CH2:33][CH2:32][C:12]2=[C:13]([N:28]3[CH2:31][CH2:30][CH2:29]3)[N:14]3[C:18]([N:19]=[C:11]2[CH2:10][CH2:9]1)=[C:17]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[CH:16]=[N:15]3)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 6797930110-Azetidin-1-yl-3-pyridin-2-ylethynyl-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohepta[f]indene-7-carboxylic acid tert-butyl ester

Product 1

HCID 6797938310-Azetidin-1-yl-3-(2-pyridin-2-yl-ethyl)-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohepta[f]indene-7-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To 87 mg (0.2 mmol) 10-azetidin-1-yl-3-pyridin-2-ylethynyl-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohepta[f]indene-7-carboxylic acid tert-butyl ester in 3 mL ethanol was added 11 mg (20% weight) palladium hydroxide, the reaction was purged 3 times with nitrogen then 3 times with hydrogen and was stirred at room temperature under a balloon of hydrogen for 16 hours. The mixture was purged twice with nitrogen, then the solution was filtered through a pad of celite. After evaporation of the solvent the product was purified by column chromatography (silica, heptane/EtOAc 9:1 to 3:7).

Workup

  1. customthe reaction was purged 3 times with nitrogen
  2. customThe mixture was purged twice with nitrogen
  3. filtrationthe solution was filtered through a pad of celite
  4. customAfter evaporation of the solvent the product
  5. customwas purified by column chromatography (silica, heptane/EtOAc 9:1 to 3:7)

Sources & evidence

ORD record
ord-63f65218df754bbeb63f46cdff7da24e
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Reaction notes

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