Ammonium formate → HCID 69435928, compound

HRID 1269984Notes

Reaction equation

HRID 1269984 reaction equation
[CH2:1]([N:8](C)[C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([O:15][C:16]2[C:17]([CH3:25])=[C:18]3[C:22](=[CH:23][CH:24]=2)[NH:21][N:20]=[CH:19]3)[CH2:10]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:1][NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([O:15][C:16]2[C:17]([CH3:25])=[C:18]3[C:22](=[CH:23][CH:24]=2)[NH:21][N:20]=[CH:19]3)[CH2:10]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69432244HCID 69432244, compound

Product 1

HCID 69435928HCID 69435928, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Under nitrogen, the N-benzyl-N-methyl-N-[cis-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexyl]amine (80 mg, 0.229 mmol) obtained in Example 729 was dissolved in ethanol (4 ml), followed by adding thereto ammonium formate (144 mg, 2.29 mmol) and then 10%-Pd/C (containing 50% water) (20 mg), and the resulting mixture was stirred with heating under reflux for 2 hours. The reaction mixture was cooled to room temperature and the Pd/C was filtered off. Then, the solvent was distilled off under reduced pressure and the resulting concentration residue was purified by a silica gel column chromatography (eluent: acetonitrile/aqueous ammonia=100/0, 100/1, 100/2, 100/4) to obtain N-methyl-N-[cis-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexyl]amine (50 mg, yield 84.2%) as a white amorphous substance.

Workup

  1. additionby adding
  2. temperaturewith heating
  3. temperatureunder reflux for 2 hours
  4. filtrationthe Pd/C was filtered off
  5. distillationThen, the solvent was distilled off under reduced pressure
  6. concentrationthe resulting concentration residue
  7. customwas purified by a silica gel column chromatography (eluent: acetonitrile/aqueous ammonia=100/0, 100/1, 100/2, 100/4)

Sources & evidence

ORD record
ord-45d1c693f221425d8437b4a8fa0f22ad
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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