Acetic Acid → HCID 178431640, compound

HRID 1269963Notes

Reaction equation

HRID 1269963 reaction equation
C=O.[CH3:3][C:4]1[C:12]([O:13][C@@H:14]2[CH2:19][CH2:18][C@H:17](N)[CH2:16][CH2:15]2)=[CH:11][C:10]([CH3:21])=[C:9]2[C:5]=1[CH:6]=[N:7][NH:8]2.[C:22]([BH3-])#[N:23].[Na+].[C:26](O)(=O)C>>[CH3:3][C:4]1[C:12]([O:13][C@@H:14]2[CH2:19][CH2:18][C@H:17]([N:23]([CH3:22])[CH3:26])[CH2:16][CH2:15]2)=[CH:11][C:10]([CH3:21])=[C:9]2[C:5]=1[CH:6]=[N:7][NH:8]2

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178431638HCID 178431638, compound

Product 1

HCID 178431640HCID 178431640, compoundYield 69.4%

Procedure

A 36% aqueous formalin solution (161 μl, 1.93 mmol) was added to a methanolic solution (2 ml) of the cis-4-[(4,7-dimethyl-1H-indazol-5-yl)oxy]cyclohexanamine (100 mg, 0.386 mmol) obtained in Example 658, and the resulting mixture was stirred at room temperature for 1 hour. Sodium cyanoborohydride (51 mg, 0.771 mmol) and acetic acid (110 μl, 1.92 mmol) were added thereto, and the resulting mixture was stirred at room temperature for 18 hours. The methanol was removed by the use of nitrogen gas and chloroform-1N-aqueous sodium hydroxide solution was added to the residue, followed by extraction with chloroform. 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 purified by a preparative thin-layer silica gel chromatography (chloroform/methanol/aqueous ammonia=7:1:0.1) to obtain cis-N-{4-[(4,7-dimethyl-1H-indazol-5-yl)oxy]cyclohexyl}-N,N-dimethylamine (77 mg, 69%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 18 hours
  2. customThe methanol was removed by the use of nitrogen gas and chloroform-1N-aqueous sodium hydroxide solution
  3. additionwas added to the residue
  4. extractionfollowed by extraction with chloroform
  5. washThe extract solution was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent, whereby a crude product
  9. customwas obtained
  10. customThe crude product was purified by a preparative thin-layer silica gel chromatography (chloroform/methanol/aqueous ammonia=7:1:0.1)

Sources & evidence

ORD record
ord-452ce2e7530f42e5b5b291788670bede
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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