Butylamine → HCID 44193226, compound

HRID 1850004Notes

Reaction equation

HRID 1850004 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].[H-].[Na+].Br[C:9]([CH3:23])([CH3:22])[C:10]([NH:12][C:13]1[CH:17]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[O:15][N:14]=1)=[O:11]>C1COCC1>[CH2:1]([NH:5][C:9]([CH3:23])([CH3:22])[C:10]([NH:12][C:13]1[CH:17]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[O:15][N:14]=1)=[O:11])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8007ButylamineHCID 24758Sodium hydrideHCID 596626262-bromo-N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-propionamide

Product 1

HCID 44193226HCID 44193226, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of n-butylamine (51 mg, 0.69 mmol) in THF (2 mL) at room temperature under nitrogen is added NaH (33 mg, 1.38 mmol) in portions over 10 min. After the addition is complete, 2-bromo-N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-propionamide (0.10 g, 0.35 mmol) is introduced to the reaction and the resulting mixture is stirred for 16 h. The solvent is then removed under reduced pressure and the residue is partitioned between DCM and saturated aqueous NaHCO3 solution. The organic phase is separated, washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The crude product is purified by mass-triggered preparative HPLC. The purified compound is dissolved in DCM and free-based with Ambersep 900-OH resin over 2 h. After this time, the suspension is filtered and the filtrate is concentrated under reduced pressure to provide the title compound (35.4 mg, 37%).

Workup

  1. additionAfter the addition
  2. customThe solvent is then removed under reduced pressure
  3. customthe residue is partitioned between DCM and saturated aqueous NaHCO3 solution
  4. customThe organic phase is separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product is purified by mass-triggered preparative HPLC
  10. dissolutionThe purified compound is dissolved in DCM and free-based with Ambersep 900-OH resin over 2 h
  11. filtrationAfter this time, the suspension is filtered
  12. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-234ed0cd34c54df38d0645c4fcf7ea4e
Source dataset
uspto-grants-2015_02
Patent number
US08957063B2

Reaction notes

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