Hydrochloric Acid → HCID 58495621, compound

HRID 1191020Notes

Reaction equation

HRID 1191020 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([CH2:9][N:10]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[CH:5][CH:4]=1)#[N:2].Cl.CCOCC>[Pd].CO>[NH2:2][CH2:1][C:3]1[N:8]=[CH:7][C:6]([CH2:9][N:10]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:11](=[O:16])[C:12]([F:13])([F:14])[F:15])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 58495553HCID 58495553, compound

Product 1

HCID 58495621HCID 58495621, compoundYield 105.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Add 6-cyano-3-[N-(cyclohexyl)-N-(2,2,2-trifluoroacetyl)-aminomethyl]-pyridine (1.5 g, 4.8 mmol), 2M hydrogen chloride in ether (7.2 mL, 14.4 mmol) and 10% Pd/C (0.3 g) to methanol (30 mL) in a pressure vessel. Flush the vessel three times with hydrogen and charge to 50 psi with hydrogen. Stir at room temperature for 4 h. Filter the mixture through Whatman® GF/B glass microfiber filter paper, and concentrate in vacuo. Purify the residue by chromatography on silica gel (100 g) eluting with a gradient of DCM to 4:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) to obtain the title compound as a clear oil (1.6 g, 99%). MS (ES+) m/z: 316 (M+H)+.

Workup

  1. customFlush the vessel three times with hydrogen
  2. additioncharge to 50 psi with hydrogen
  3. filtrationFilter the mixture through Whatman® GF/B glass microfiber
  4. filtrationfilter paper
  5. concentrationconcentrate in vacuo
  6. customPurify the residue by chromatography on silica gel (100 g)
  7. washeluting with a gradient of DCM to 4:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2)

Sources & evidence

ORD record
ord-49790f40905e4b29b3a307499bd8b604
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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