Sodium Cyanide → HCID 45138012, compound

HRID 1698162Notes

Reaction equation

HRID 1698162 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]=[CH:14][N:13]=[C:12]([CH2:17][OH:18])[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[F:19][C:20]([F:30])([F:29])[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][NH2:25].[C-]#N.[Na+]>C1COCC1.[O-2].[Mn+4].[O-2]>[F:19][C:20]([F:29])([F:30])[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][NH:25][C:17]([C:12]1[C:11]2[CH:10]=[N:9][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:16]=2[CH:15]=[CH:14][N:13]=1)=[O:18]

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 759623-(Trifluoromethyl)benzylamineHCID 59278490HCID 59278490, compound

Product 1

HCID 45138012HCID 45138012, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture [1-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]-methanol (20 mg, 0.08 mmol), 3-trifluoromethylbenzylamine (71 mg, 0.41 mmol) and sodium cyanide (4 mg, 0.08 mmol) in THF (2 mL) was added manganese (IV) oxide (107 mg, 1.23 mmol). After 30 minutes, additional manganese (IV) oxide (107 mg, 1.23 mmol) was added. After 18 hours, the reaction was filtered through a pad of diatomaceous earth and concentrated in vacuo. The mixture was purified by silica gel chromatography eluting with a gradient of 0-5% methanol in dichloromethane to afford the title compound as a yellow solid.

Workup

  1. waitAfter 18 hours
  2. filtrationthe reaction was filtered through a pad of diatomaceous earth
  3. concentrationconcentrated in vacuo
  4. customThe mixture was purified by silica gel chromatography
  5. washeluting with a gradient of 0-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-d763f6bf228b4638b13f9dc2edde2848
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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