tert-Butyl 4-(2-(hydroxymethyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-Butyl 4-(2-(hydroxymethyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)piperidine-1-carboxylate

HRID 1772648Notes

Reaction equation

HRID 1772648 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:9][CH:8]=[C:7]([C:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]=3)[N:6]2[CH:30]=1>CO.[Pd]>[OH:1][CH2:2][C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)=[N:9][CH:8]=[C:7]([CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:19][CH2:18]3)[N:6]2[CH:30]=1

Participants

4

Reactant 1

HCID 117733768tert-Butyl 4-(2-(hydroxymethyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 117733759tert-Butyl 4-(2-(hydroxymethyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 26a (390 mg, 0.93 mmol) in MeOH (250 mL) was hydrogenated over 10% Pd/C in a continuous-flow hydrogenation reactor. The solvents were removed and the residue was dissolved in DCM, dried over Na2SO4, filtered, and concentrated to obtain compound 26b. Mass Spectrum (LCMS, ESI pos.) Calcd. for C21H31N5O4: 418.2 (M+H). Found 418.3.

Workup

  1. customThe solvents were removed
  2. dissolutionthe residue was dissolved in DCM
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ca5e9ac192e34801b0300bcd2363ab9c
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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