Nonane → HCID 21906743, compound

HRID 1247609Notes

Reaction equation

HRID 1247609 reaction equation
[CH2:1]([N:4](C)[C:5](=O)OC(C)(C)C)[CH:2]=[CH2:3].CCCCCCCCC.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:30]12([CH2:40][NH:41][C:42](=[O:51])[C:43]3[C:48]([Cl:49])=[CH:47][N:46]=[C:45](Br)[CH:44]=3)[CH2:39][CH:34]3[CH2:35][CH:36]([CH2:38][CH:32]([CH2:33]3)[CH2:31]1)[CH2:37]2>O1CCCC1.O.CN(C)C=O.[Cl-].[Na+].O>[ClH:49].[C:30]12([CH2:40][NH:41][C:42](=[O:51])[C:43]3[C:48]([Cl:49])=[CH:47][N:46]=[C:45]([CH2:3][CH2:2][CH2:1][NH:4][CH3:5])[CH:44]=3)[CH2:39][CH:34]3[CH2:35][CH:36]([CH2:38][CH:32]([CH2:33]3)[CH2:31]1)[CH2:37]2

Participants

9

Reactant 4

HCID 8141NonaneHCID 62657Potassium Phosphate, TribasicHCID 10241245169268-90-0HCID 11773529N-(1-adamantylmethyl)-2-bromo-5-chloroisonicotinamide

Product 1

HCID 21906743HCID 21906743, compoundYield 70.7%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl allyl(methyl)carbamate (0.27 g) in 9-boroabicyclo[3.3.1]nonane (6.24 ml of a 0.5M solution in tetrahydrofuran) was heated at reflux under nitrogen for 4 hours. The solution was cooled to 0° C. and potassium phosphate (1.5 mI of a 3M solution in water) was added. The mixture was stirred for 15 minutes and a solution of N-(1-adamantylmethyl)-2-bromo-5-chloroisonicotinamide (Example 1(ii)) (0.50 g) and dichloro[1,1′-bis(diphenylphosphino)ferrocenyl]palladium (II) (0.045 g) in anhydrous N,N-dimethylformamide (4 ml) was added. The mixture was heated at 60° C. under nitrogen for 3 hours, diluted with saturated brine (25 ml) and extracted into ethyl acetate (3×25 ml). The combined extracts were dried over anhydrous sodium sulphate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with iso-hexane:ethyl acetate (6:1 to 1.5:1). The isolated material (0.50 g) was dissolved in a solution of hydrogen chloride in 1,4-dioxane (10 ml of a 4M solution) and concentrated; the resultant solid was recrystallised from 1,4-dioxane/methanol and the solid collected by is filtration to afford the titled compound (0.19 g) as a colourless powder.

Workup

  1. temperatureat reflux under nitrogen for 4 hours
  2. temperatureThe mixture was heated at 60° C. under nitrogen for 3 hours
  3. extractionextracted into ethyl acetate (3×25 ml)
  4. dry with materialThe combined extracts were dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel eluting with iso-hexane:ethyl acetate (6:1 to 1.5:1)
  8. dissolutionThe isolated material (0.50 g) was dissolved in a solution of hydrogen chloride in 1,4-dioxane (10 ml of a 4M solution) and
  9. concentrationconcentrated
  10. customthe resultant solid was recrystallised from 1,4-dioxane/methanol
  11. customthe solid collected
  12. filtrationfiltration

Sources & evidence

ORD record
ord-918208719a24423f97c7a8c4298ee06a
Source dataset
uspto-grants-2006_10
Patent number
US07129246B2

Reaction notes

Loading…