Sodium Hydroxide → HCID 178442003, compound

HRID 493499Notes

Reaction equation

HRID 493499 reaction equation
[CH2:1]([N:8]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]#[N:40])=[C:33]([Br:41])[CH:32]=2)=[CH:27][CH:26]=1)[C:9]([C:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][C:12]=1[CH2:20][CH2:21][CH2:22][CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:42]=[N+:43]=[N-:44].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C=O)C.O>[CH2:1]([N:8]([CH2:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]3[NH:44][N:43]=[N:42][N:40]=3)=[C:33]([Br:41])[CH:32]=2)=[CH:29][CH:30]=1)[C:9]([C:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][C:12]=1[CH2:20][CH2:21][CH2:22][CH3:23])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 68861317HCID 68861317, compound

Product 1

HCID 178442003HCID 178442003, compoundYield 43.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-benzyl-N-{[3′-bromo-4′-(cyanomethoxy)-1,1′-biphenyl-4-yl]methyl}-2-butyl-1-benzofuran-3-carboxamide (800 mg, 1.3 mmol), prepared in the previous step, sodium azide (320 mg, 4.9 mmol) and ammonium chloride (264 mg, 4.9 mmol) in 40 mL of DMF was stirred under nitrogen at 100° C. for 3.5 h. By TLC some starting material remained. An additional 320 mg (4.9 mmol) of sodium azide and 264 mg (4.9 mmol) of ammonium chloride were added and the reaction was stirred at 100° C. for 4 h. The reaction was diluted with water, made basic by the addition of 1 N NaOH and partitioned with ethyl acetate. The organic layer was separated and the aqueous layer extracted multiple times with ethyl acetate. By TLC the product was in the ethyl acetate layer. The ethyl acetate solution was concentrated. The residue was dissolved in methylene chloride and acidified with 1 N HCl. The organic layer was separated, extracted three times with water, dried (MgSO4) and the solvent removed under reduced pressure to give the title compound (370 mg, 43%) as a white solid, MS (ESI) m/z 650 [M+H]+. Elemental Analysis for C35H32BrN5O3.0.34 H2O: Calc'd: C, 64.01; H, 5.02; N, 10.66; Found: C, 62.18; H, 5.32; N:9.50

Workup

  1. stirringthe reaction was stirred at 100° C. for 4 h
  2. custompartitioned with ethyl acetate
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted multiple times with ethyl acetate
  5. concentrationThe ethyl acetate solution was concentrated
  6. dissolutionThe residue was dissolved in methylene chloride
  7. customThe organic layer was separated
  8. extractionextracted three times with water
  9. dry with materialdried (MgSO4)
  10. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-af665ec8467b45e99b10c69ba98e25dc
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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