Sodium Cyanide → HCID 57441162, compound

HRID 1517107Notes

Reaction equation

HRID 1517107 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[O:9])[C:5]([CH3:21])=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1.[C-:32]#[N:33].[Na+]>CN1CCCC1=O>[CH3:21][C:5]1[CH:4]=[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[C:2]([C:32]#[N:33])=[N:7][C:6]=1[C:8]([N:10]1[CH2:15][CH2:14][CH:13]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:12][CH2:11]1)=[O:9]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 44547211[6-Chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Product 1

HCID 57441162HCID 57441162, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A well stirred suspension of 0.30 g (0.66 mmol) of [6-chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 3) and 0.098 g (2.0 mmol) of sodium cyanide in 5.0 ml of 1-methyl-pyrrolidin-2-one was heated for 16 hours at 150° C. After cooling down to RT, the reaction mixture was poured into crashed ice/NaCl-solution (sat. in H2O) and extracted three times with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1) to give 0.086 g (29%) of 5-methyl-6-(4-pyrrolidin-1-yl-piperidine-1-carbonyl)-3-(3-trifluoromethyl-phenyl)-pyridine-2-carbonitrile as light yellow solid. MS: 443.4 (MH+); and 0.045 g (15%) of 5-methyl-6-(4-pyrrolidin-1-yl-piperidine-1-carbonyl)-3-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid amide as light yellow solid. MS: 461.4 (MH+).

Workup

  1. temperatureAfter cooling down to RT
  2. additionthe reaction mixture was poured
  3. extractionextracted three times with CH2Cl2
  4. washthe organic phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1)

Sources & evidence

ORD record
ord-143bef42013a4d2c836c9fc3daa43668
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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