Sodium Hydroxide → HCID 178482640, compound

HRID 493495Notes

Reaction equation

HRID 493495 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([N:19]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]#[N:37])=[C:30]([Br:38])[CH:29]=3)=[CH:24][CH:23]=2)[CH3:20])=[O:18])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:39]=[N+:40]=[N-:41].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C=O)C.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([N:19]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]4[NH:41][N:40]=[N:39][N:37]=4)=[C:30]([Br:38])[CH:29]=3)=[CH:24][CH:23]=2)[CH3:20])=[O:18])=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68860117HCID 68860117, compound

Product 1

HCID 178482640HCID 178482640, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-benzyl-N-{[3′-bromo-4′-(cyanomethoxy)-1,1′-biphenyl-4-yl]methyl}-N-methyl-1H-indole-3-carboxamide (1.56 g, 2.76 mmol), prepared in the previous step, sodium azide (542 mg, 8.34 mmol) and ammonium chloride (446 mg, 8.33 mmol) in 30 mL of DMF was stirred under nitrogen at 100° C. for 6 h. After cooling to room temperature the reaction was diluted with 50 mL of water, made basic by the addition of 10 mL of 1 N NaOH and extracted five times with ethyl acetate. The aqueous layer was filtered and then acidified with 20 mL of 1 N HCl. An oil precipitated. The aqueous layer was decanted and the oil partitioned between methylene chloride and water. The organic layer was separated, dried (MgSO4) and the solvent removed under reduced pressure to give the title compound (1.22 g, 72%) as a light yellow foam, MS (ESI) m/z 607 [M+H]+. Elemental Analysis for C32H27BrN6O2.0.08 H2O: Calc'd: C, 63.12; H, 4.50; N, 13.80; Found: C, 61.37; H, 4.65; N, 12.89.

Workup

  1. temperatureAfter cooling to room temperature the reaction
  2. extractionextracted five times with ethyl acetate
  3. filtrationThe aqueous layer was filtered
  4. customAn oil precipitated
  5. customThe aqueous layer was decanted
  6. customthe oil partitioned between methylene chloride and water
  7. customThe organic layer was separated
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-837dd222323641ee9d945eca502f3ae2
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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