Benzaldehyde → HCID 18447429, compound

HRID 1269900Notes

Reaction equation

HRID 1269900 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:23]12[NH:30][CH:27]([CH2:28][CH2:29]1)[CH2:26][CH:25]([NH:31][C:32]1[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=1)[NH:37][N:36]=[CH:35]3)[CH2:24]2>ClCCl>[CH2:1]([N:30]1[CH:27]2[CH2:28][CH2:29][CH:23]1[CH2:24][CH:25]([NH:31][C:32]1[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=1)[NH:37][N:36]=[CH:35]3)[CH2:26]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 18447426HCID 18447426, compound

Product 1

HCID 18447429HCID 18447429, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzaldehyde (37 μl, 0.364 mmol) and sodium triacetoxyborohydride (127 mg, 0.599 mmol) were added to a suspension of the N-(8-azabicyclo[3.2.1]oct-3-yl)-1H-indazol-5-amine (73 mg, 0.301 mmol) obtained in Example 525 in dichloromethane (1 ml), and the resulting mixture was stirred at room temperature for 25 hours. The reaction was terminated by the addition of a saturated aqueous sodium hydrogencarbonate solution, followed by extraction with ethyl acetate. The extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby a crude product was obtained. The crude product was washed with cold methanol and collected by filtration to obtain N-(8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)-1H-indazol-5-amine (52 mg, 52%).

Workup

  1. customThe reaction was terminated by the addition of a saturated aqueous sodium hydrogencarbonate solution
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract solution was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent, whereby a crude product
  7. customwas obtained
  8. washThe crude product was washed with cold methanol
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-eaf50e8ad280478ca40a976256d1febd
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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