Hydrochloric Acid → HCID 22036090, compound

HRID 1789923Notes

Reaction equation

HRID 1789923 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1.C([Li])CCC.CON(C)[C:23](=[O:27])[CH2:24][CH2:25][CH3:26].Cl.C(=O)([O-])O.[Na+]>C(OCC)C>[C:23]([C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1)(=[O:27])[CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 13704543N-Methoxy-N-methylbutyramideHCID 15461537N-(5-bromopyridin-2-yl)-2,2-dimethylpropanamideHCID 178418339Butyllithium

Product 1

HCID 22036090HCID 22036090, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N-(5-bromopyridin-2-yl)-2,2-dimethyl-propionamide (3.582 g, 13.9 mmol) in diethyl ether (36 mL) was cooled to −78° C. under argon and n-butyllithium (1.6 M, 19 mL, 30.4 mmol) was added dropwise within 20 min. 5 min after complete addition the mixture was allowed to warm up to 0° C. N-Methoxy-N-methyl butyramide (3.65 g, 27.8 mmol) was added within less than 5 min and stirring was continued for 45 min. The clear solution was acidified with 2 N hydrochloric acid to pH 2. After vigorous stirring for 15 min the mixture was neutralised with sodium hydrogen carbonate and the layers were separated. The aqueous layer was extracted three times with diethyl ether. The combined organic layers were washed with brine, dried and concentrated under reduced pressure. The resulting oil was dried in oil pump vacuum to remove the excess reagent. After flash chromatography (dichloromethane/methanol 60:1) crude N-(5-butyryl-pyridin-2-yl)-2,2-dimethyl-propionamide (2.47 g, 71%) was obtained as a light orange oil which was not purified further.

Workup

  1. addition5 min after complete addition the mixture
  2. stirringAfter vigorous stirring for 15 min the mixture
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted three times with diethyl ether
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting oil was dried in oil pump vacuum
  9. customto remove the excess reagent

Sources & evidence

ORD record
ord-0b93bfa366994cbcb9be4fd35009ee6f
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

Loading…