Potassium Carbonate → HCID 18771354, compound

HRID 479592Notes

Reaction equation

HRID 479592 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[C:5](=[O:23])[C:6]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)=[CH:7][NH:8]2.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:31][CH2:32][CH2:33][C:34]#[N:35]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[C:5](=[O:23])[C:6]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)=[CH:7][N:8]2[CH2:31][CH2:32][CH2:33][C:34]#[N:35]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123364-ChlorobutyronitrileHCID 18771392HCID 18771392, compound

Product 1

HCID 18771354HCID 18771354, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

400 mg (1.28 mmol) of compound 29 are added to 10 ml of anhydrous N,N-dimethylformamide under a nitrogen atmosphere. 1.35 g of anhydrous potassium carbonate (7.5 eq) and then 0.35 ml of 4-chlorobutyronitrile (3 eq) are successively added to this suspension. The reaction is stirred at 90° C. for 18 hours. The solvents are evaporated off. The residue is taken up in CH2Cl2 and washed twice with water. The organic phase is dried over MgSO4 and then evaporated under reduced pressure. The residue obtained is purified by chromatography on a column of silica treated with triethylamine (eluent: 7/3 CH2Cl2/EtOAc) to give 180 mg (37%) of compound 80 and 274 mg (56%) of derivative 81.

Workup

  1. customThe solvents are evaporated off
  2. washwashed twice with water
  3. dry with materialThe organic phase is dried over MgSO4
  4. customevaporated under reduced pressure
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. additiontreated with triethylamine (eluent: 7/3 CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-4d3366171795403e8f4eacd4968286de
Source dataset
uspto-grants-2003_11
Patent number
US06645983B1

Reaction notes

Loading…