HCID 86706464, compound → HCID 86706463, compound

HRID 919593Notes

Reaction equation

HRID 919593 reaction equation
[CH3:1][Si:2]([CH3:34])([CH3:33])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2=[N:12][CH:13]=[N:14][C:15]([O:16][C@H:17]3[CH2:22][CH2:21][CH2:20][N:19](C(OCC4C=CC=CC=4)=O)[CH2:18]3)=[C:10]2[CH:9]=[N:8]1.[H][H]>CCO.[Pd]>[NH:19]1[CH2:20][CH2:21][CH2:22][C@H:17]([O:16][C:15]2[N:14]=[CH:13][N:12]=[C:11]3[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:34])([CH3:33])[CH3:1])[N:8]=[CH:9][C:10]=23)[CH2:18]1

Participants

5

Reactant 2

HCID 86706464HCID 86706464, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86706463HCID 86706463, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (S)-benzyl 3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)piperidine-1-carboxylate (200 mg, 0.41 mmol) in EtOH (10 mL) was added 10% Pd/C (40 mg) and the solution was placed under an atomsphere of hydrogen (1 psi). The reaction mixture was purged with nitrogen and filtered through a Celite pad, and the filtrate was evaporated in vacuo to give (115 mg, 79%) the titled compound which was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ 8.63 and 8.60 (2s, 1H), 8.31-8.21 (2s, 1H), 5.72 and 5.70 (2s, 2H), 5.38-5.22 (m, 1H), 3.63-3.59 (m, 2H), 3.21-3.07 (m, 1H), 2.81-2.63 (m, 2H), 2.23-2.01 (m, 2H), 1.79-1.61 (m, 2H), 1.58-1.45 (m, 2H), 0.85 (t, J=6.4 Hz, 2H), −0.91 (s, 9H). LC-MS: m/z [M+1]=350.

Workup

  1. customThe reaction mixture was purged with nitrogen
  2. filtrationfiltered through a Celite pad
  3. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-9e6ff1e6e3f040838a348e2d72ec1d79
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

Loading…