Acetic Acid → HCID 59326822, compound

HRID 1880067Notes

Reaction equation

HRID 1880067 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:8]([O:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]4[NH:25][C:24]5[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=5[N:22]=4)=[CH:16][CH:15]=3)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.C(O)(=O)C>C1COCC1.[Pd]>[O:1]1[CH2:2][CH2:3][CH:4]([C:7]2[C:8]([O:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]4[NH:22][C:23]5[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=5[N:25]=4)=[CH:16][CH:15]=3)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59326932HCID 59326932, compound

Product 1

HCID 59326822HCID 59326822, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranCatalystHCID 23938PalladiumCatalyst

Procedure

To a round bottomed flask was added N-(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine (0.0784 g, 0.204 mmol), palladium, 10% wt. on activated carbon (0.043 g, 0.041 mmol), and acetic acid (0.023 mL, 0.408 mmol) in THF (a few drops of MeOH was added to help solubility). To remove oxygen from the round bottomed flask, the flask was flushed by nitrogen and the placed under vacuum repeatedly. Hydrogen gas was then introduced to the reaction and allowed to stir. Upon completion, the reaction was filtered through celite. The crude product was run through a SCX cartridge. Impurities were removed from column using DCM and MeOH. The product was flushed from the cartridge using 2.0 ammonia in MeOH to provide N-(4-(3-(Tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine. MS (ESI, pos. ion) m/z: 387.0 (M+1). IC50 (uM) +++++.

Workup

  1. customTo remove oxygen from the round bottomed flask
  2. customthe flask was flushed by nitrogen
  3. additionHydrogen gas was then introduced to the reaction
  4. filtrationUpon completion, the reaction was filtered through celite
  5. customImpurities were removed from column
  6. customThe product was flushed from the cartridge

Sources & evidence

ORD record
ord-51fe4bff0fea437397b03c57acdfe600
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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