Diisopropylamine → HCID 67518348, compound

HRID 2175912Notes

Reaction equation

HRID 2175912 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[C:8]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[N:7]=[CH:6][C:5]=1[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC>O1CCCC1>[CH3:13][C:12]([CH3:15])([CH3:14])[C:11]([NH:10][C:8]1[N:7]=[CH:6][C:5]2[CH:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:2][CH2:3][C:4]=2[CH:9]=1)=[O:16]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 86727103HCID 86727103, compoundHCID 178418339Butyllithium

Product 1

HCID 67518348HCID 67518348, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyl {4-(2-bromoethyl)-6-[(2,2-dimethylpropanoyl)amino]pyridin-3-yl}acetate (6.5 g, 16.3 mmol) in tetrahydrofuran (50 mL) cooled in a dry ice-acetone bath was treated with a solution of lithium diisopropylamide in tetrahydrofuran (50 mL) (prepared from diisopropylamine (3.79 g, 34.7 mmol) and n-butyllithium (2.5 M, 13.7 mL) dropwise via addition funnel over 1 h. After complete addition, the reaction stirred an additional 1 h, then was quenched with saturated sodium bicarbonate solution and allowed to warm to room temperature. The resulting mixture was diluted with ethyl acetate and water and transferred to a separatory funnel. The layers were separated and the aqueous extracted with ethyl acetate (2×). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the resulting residue (2->25% EtOAc/hexanes eluent) provided the title compound. LC/MS (M+1)+=319.0.

Workup

  1. additionAfter complete addition
  2. customwas quenched with saturated sodium bicarbonate solution
  3. additionThe resulting mixture was diluted with ethyl acetate and water
  4. customtransferred to a separatory funnel
  5. customThe layers were separated
  6. extractionthe aqueous extracted with ethyl acetate (2×)
  7. washThe combined organics were washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification of the resulting residue (2->25% EtOAc/hexanes eluent)

Sources & evidence

ORD record
ord-d41cbcae8328472ba575c47713eed9eb
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

Loading…