Potassium tert-butoxide → HCID 58133378, compound

HRID 1042317Notes

Reaction equation

HRID 1042317 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[N:10]([C:12](=[O:25])[CH2:13][C:14]1[C:19]([CH2:20][CH3:21])=[CH:18][C:17]([CH3:22])=[CH:16][C:15]=1[CH2:23][CH3:24])[CH3:11].CC(C)([O-])C.[K+]>CN(C)C=O>[CH2:20]([C:19]1[CH:18]=[C:17]([CH3:22])[CH:16]=[C:15]([CH2:23][CH3:24])[C:14]=1[C:13]1[C:12](=[O:25])[N:10]([CH3:11])[C:5]2[C:4]([C:3]=1[OH:2])=[CH:9][CH:8]=[CH:7][N:6]=2)[CH3:21]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 58133380HCID 58133380, compound

Product 1

HCID 58133378HCID 58133378, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-{[2-(2,6-diethyl-4-methyl-phenyl)-acetyl]-methyl-amino}-nicotinic acid methyl ester (300 mg) in N,N-dimethylformamide (5 ml) was added potassium tert-butoxide (250 mg). The reaction mixture was stirred at ambient temperature for 18 hours, and then at 50° C. for 2 hours. The reaction mixture was partitioned the reaction between water and dichloromethane. The phases were separated and the aqueous phase was extracted with further dichloromethane and ethyl acetate. The aqueous phase was acidified by addition of aqueous hydrochloric acid (2M) and extracted three times with ethyl acetate. The combined organic extracts were dried over magnesium sulfate and concentrated. The residue was passed through a plug of silica eluting with ethyl acetate to give Compound No. D20 of Table D as an off-white solid (320 mg).

Workup

  1. waitat 50° C. for 2 hours
  2. customThe reaction mixture was partitioned
  3. customthe reaction between water and dichloromethane
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with further dichloromethane and ethyl acetate
  6. additionThe aqueous phase was acidified by addition of aqueous hydrochloric acid (2M)
  7. extractionextracted three times with ethyl acetate
  8. dry with materialThe combined organic extracts were dried over magnesium sulfate
  9. concentrationconcentrated
  10. customto give Compound No

Sources & evidence

ORD record
ord-3522a1d9ae62482d8229d41c69af4b0b
Source dataset
uspto-grants-2013_10
Patent number
US08557840B2

Reaction notes

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