HCID 67959790, compound → HCID 67959847, compound

HRID 1529405Notes

Reaction equation

HRID 1529405 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[N:12]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[N:11]=[C:10]3[C:22]2[N:27]=[C:26]([O:28][C@H:29]3[CH2:36][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:34][CH2:33][C:30]43[CH2:32][CH2:31]4)[CH:25]=[N:24][CH:23]=2)[CH2:3][CH2:2]1>[Pd].CCO>[O:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:16]1[N:12]1[C:13]2[C:9](=[CH:8][C:7]([CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:15][CH:14]=2)[C:10]([C:22]2[N:27]=[C:26]([O:28][C@H:29]3[CH2:36][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:34][CH2:33][C:30]43[CH2:32][CH2:31]4)[CH:25]=[N:24][CH:23]=2)=[N:11]1

Participants

4

Reactant 1

HCID 67959790HCID 67959790, compound

Product 1

HCID 67959847HCID 67959847, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on carbon, 10% (35.1 mg, 0.330 mmol) was added to a solution of (4R)-tert-butyl 4-(6-(5-(3,6-dihydro-2H-pyran-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)pyrazin-2-yloxy)-6-azaspiro[2.5]octane-6-carboxylate (194 mg, 0.330 mmol) in EtOH (3.3 mL) at RT in a portable hydrogen reactor; the reaction was stirred under 45 psi of H2 for 1.5 h. The mixture was filtered through a pad of Celite, washed with DCM and MeOH, and concentrated to give (4R)-tert-butyl 4-(6-(1-(tetrahydro-2H-pyran-2-yl)-5-(tetrahydro-2H-pyran-4-yl)-1H-indazol-3-yl)pyrazin-2-yloxy)-6-azaspiro[2.5]octane-6-carboxylate (180 mg, 0.305 mmol, 92% yield) as an amber oil. MS (ESI, pos. ion) m/z: 590.4 (M+1).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washwashed with DCM and MeOH
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-44d36cc5e19c49478fd538441ac72c2f
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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