HCID 57478051, compound → HCID 66597687, compound

HRID 1962825Notes

Reaction equation

HRID 1962825 reaction equation
[C:1]([CH2:3][CH:4]([CH:27]1[CH2:31][CH2:30][N:29](C(OCC2C=CC=CC=2)=O)[CH2:28]1)[N:5]1[CH:9]=[C:8]([C:10]2[C:11]3[CH:18]=[CH:17][N:16]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:12]=3[N:13]=[CH:14][N:15]=2)[CH:7]=[N:6]1)#[N:2]>CO.[Pd]>[NH:29]1[CH2:30][CH2:31][CH:27]([CH:4]([N:5]2[CH:9]=[C:8]([C:10]3[C:11]4[CH:18]=[CH:17][N:16]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:26])[CH3:25])[C:12]=4[N:13]=[CH:14][N:15]=3)[CH:7]=[N:6]2)[CH2:3][C:1]#[N:2])[CH2:28]1

Participants

4

Reactant 1

HCID 57478051HCID 57478051, compound

Product 1

HCID 66597687HCID 66597687, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

Benzyl 3-{2-cyano-1-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidine-1-carboxylate (161 mg, 0.282 mmol) was dissolved in methanol (5 mL), and a catalytic amount of 5% Pd—C was added. The suspension was stirred at ambient temperature for 1 hour under an atmosphere of hydrogen provided by a balloon. A catalytic amount of 10% Pd—C was then added, and the reaction stirred for 2 hours under an atmosphere of hydrogen provided by a balloon. The mixture was then filtered, and purified via preparative-HPLC/MS (C18 eluting with a gradient of H2O and ACN containing 0.15% NH4OH) to afford the product as a mixture of diastereomers (57 mg, 46%).

Workup

  1. customprovided by a balloon
  2. stirringthe reaction stirred for 2 hours under an atmosphere of hydrogen
  3. customprovided by a balloon
  4. filtrationThe mixture was then filtered
  5. custompurified via preparative-HPLC/MS (C18
  6. washeluting with a gradient of H2O and ACN containing 0.15% NH4OH)
  7. customto afford the product
  8. additionas a mixture of diastereomers (57 mg, 46%)

Sources & evidence

ORD record
ord-ea1d1931d3d84e14bcab97be73acc3ca
Source dataset
uspto-grants-2013_04
Patent number
US08415362B2

Reaction notes

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