Pyridine → 6-Chloro-5-cyclopropyl-2-(4-oxopentyloxy)nicotinonitrile

HRID 2284504

Reaction equation

HRID 2284504 reaction equation
[Cl:1][C:2]1[C:10]([CH:11]2[CH2:13][CH2:12]2)=[CH:9][C:5]([C:6]([NH2:8])=O)=[C:4]([O:14][CH2:15][CH2:16][CH2:17][C:18](=[O:20])[CH3:19])[N:3]=1.O=P(Cl)(Cl)Cl.N1C=CC=CC=1.C([O-])(O)=O.[Na+]>C(#N)C>[Cl:1][C:2]1[C:10]([CH:11]2[CH2:12][CH2:13]2)=[CH:9][C:5]([C:6]#[N:8])=[C:4]([O:14][CH2:15][CH2:16][CH2:17][C:18](=[O:20])[CH3:19])[N:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 866617286-Chloro-5-cyclopropyl-2-(4-oxopentyloxy)nicotinamide

Product 1

HCID 866617296-Chloro-5-cyclopropyl-2-(4-oxopentyloxy)nicotinonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-chloro-5-cyclopropyl-2-(4-oxopentyloxy)nicotinamide (298 mg, 1 mmol) in acetonitrile (20 mL) was added POCl3 (460 mg, 3 mmol) and pyridine (474 mg, 6 mmol). After stirred at r.t for 2 hrs, the mixture was poured into aq. NaHCO3, extracted with EtOAc. The separated organics was dried and concentrated in vacuo to afford 6-chloro-5-cyclopropyl-2-(4-oxopentyloxy)nicotinonitrile. (300 mg).

Workup

  1. extractionextracted with EtOAc
  2. customThe separated organics was dried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56f71123d6f04dca91f2ce32a39b6313
Source dataset
uspto-grants-2015_09
Patent number
US09145429B2

Linked notes

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