Hydrochloric Acid → HCID 11163675, compound

HRID 505447Notes

Reaction equation

HRID 505447 reaction equation
[Li][CH2:2]CCC.[CH2:6]([C:13]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:14]=1[C:15]([NH:17][CH3:18])=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1CCl.Cl>C1COCC1>[CH3:24][O:23][C:21]1[CH:22]=[C:13]2[C:14](=[CH:19][CH:20]=1)[C:15](=[O:16])[N:17]([CH3:2])[C:18]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][N:25]=1)=[C:6]2[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 23393Picolyl chlorideHCID 225559272-Benzyl-4-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 11163675HCID 11163675, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-BuLi (1.6 M in hexanes, 17.6 mL, 28 mmol) was added to a solution of amide 9 (3 g, 12 mmol) in THF (70 mL) at −78 C. After stirring for 30 min, 2-picolyl chloride.HCl (3.1 g, 8.8 mmol) was added. After stirring for 30 min the reaction mixture was quenched with water then warmed to room temperature. The reaction mixture was concentrated and the residue partitioned between water and EtOAc. The organic phase was dried (Na2SO4) and concentrated. The residue was purified by flash chromatography.

Workup

  1. stirringAfter stirring for 30 min the reaction mixture
  2. customwas quenched with water
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue partitioned between water and EtOAc
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-264d22103efe4d038a6fa708576f5363
Source dataset
uspto-grants-2010_08
Patent number
US07781457B2

Reaction notes

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