2-Amino-2-methyl-1-propanol → HCID 89544560, compound

HRID 2283435Notes

Reaction equation

HRID 2283435 reaction equation
Br[CH:2]([C:5]1[C:6]([F:20])=[C:7]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])[C:8]([Cl:11])=[CH:9][CH:10]=1)[CH2:3][CH3:4].[CH3:21][C:22]([NH2:26])([CH3:25])[CH2:23][OH:24]>CN(C=O)C>[C:12]([C:7]1[C:6]([F:20])=[C:5]([CH:2]([NH:26][C:22]([CH3:25])([CH3:21])[CH2:23][OH:24])[CH2:3][CH3:4])[CH:10]=[CH:9][C:8]=1[Cl:11])(=[O:13])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 89544562HCID 89544562, compound

Product 1

HCID 89544560HCID 89544560, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Step 3 A solution of [3-(1-bromo-propyl)-6-chloro-2-fluoro-phenyl]-phenyl-methanone (50 mg; 0.14 mmol) and 2-methyl-2-aminopropanol (30 μl; 2 equiv.) in DMF (1 ml) was stirred at room temperature for 72 hours then partitioned between Et2O and brine. The Et2O later was separated, dried (Na2SO4), filtered and evaporated. The crude material was purified by flash column chromatography using gradient elution from 0-10% MeOH/DCM. Product containing fractions were combined, treated with saturated HCl/EtOAc then evaporated. The residue was triturated with Et2O, the solid collected by filtration, washed with Et2O and sucked dry to give 55 mg of 2-{[1-(3-benzoyl-4-chloro-2-fluorophenyl)-propyl]amino}-2-methylpropan-1-ol as a white solid.

Workup

  1. customthen partitioned between Et2O and brine
  2. customThe Et2O later was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude material was purified by flash column chromatography
  7. washelution from 0-10% MeOH/DCM
  8. additionProduct containing fractions
  9. additiontreated with saturated HCl/EtOAc
  10. customthen evaporated
  11. customThe residue was triturated with Et2O
  12. filtrationthe solid collected by filtration
  13. washwashed with Et2O
  14. customsucked dry

Sources & evidence

ORD record
ord-513d4c4272084bf785b412a86045efd0
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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