HCID 49764568, compound → HCID 49764569, compound

HRID 2188550Notes

Reaction equation

HRID 2188550 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5](=[O:35])[N:6]([CH:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:17][CH:16]([NH:18][C:19]([CH2:21][NH:22][C:23](=[O:34])[C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=4)=[O:20])[CH2:15]3)[CH2:10][CH2:9]2)[CH:7]=1>CO.[Pd]>[O:35]=[C:5]1[N:4]=[CH:3][CH:2]=[CH:7][N:6]1[CH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:15][CH:16]([NH:18][C:19]([CH2:21][NH:22][C:23](=[O:34])[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:32])([F:33])[F:31])[CH:25]=3)=[O:20])[CH2:17]2)[CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 49764568HCID 49764568, compound

Product 1

HCID 49764569HCID 49764569, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-({1-[4-(5-Bromo-2-oxo-2H-pyrimidin-1-yl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide (as prepared in Example 3, Step C, ˜150 mg, 0.27 mmol) in MeOH (20 mL) was driven through H-Cube® Continuous-flow Hydrogenation reactor (ThalesNano, Budapest, Hungary) under full hydrogen mode at room temperature using 10% Pd/C cartridge. The resulting solution was concentrated and purified by silica gel column on a CombiFlash® system using ethyl acetate and 7N NH3 in MeOH as eluent (from pure ethyl acetate to 5% 7N NH3 in MeOH in ethyl acetate) to afford the title compound as white solid.

Workup

  1. customat room temperature
  2. concentrationThe resulting solution was concentrated
  3. custompurified by silica gel column on a CombiFlash® system

Sources & evidence

ORD record
ord-5ebcdeb866fa4b4880e64ae1762a0ea6
Source dataset
uspto-grants-2012_12
Patent number
US08324186B2

Reaction notes

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