Acetic Acid → HCID 18447432, compound

HRID 1269875Notes

Reaction equation

HRID 1269875 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[CH3:19][C:20]1[C:28]([NH2:29])=[CH:27][CH:26]=[C:25]2[C:21]=1[CH:22]=[N:23][N:24]2[CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1.[CH2:36]([N:43]1[CH:48]2[CH2:49][CH2:50][CH:44]1[CH2:45][C:46](=O)[CH2:47]2)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(=O)([O-])O.[Na+]>ClCCCl>[CH2:36]([N:43]1[CH:48]2[CH2:49][CH2:50][CH:44]1[CH2:45][CH:46]([NH:29][C:28]1[C:20]([CH3:19])=[C:21]3[C:25](=[CH:26][CH:27]=1)[N:24]([CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1)[N:23]=[CH:22]3)[CH2:47]2)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 1198468-Benzyl-8-azabicyclo(3.2.1)octan-3-oneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 694312064-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-amine

Product 1

HCID 18447432HCID 18447432, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (477 mg, 2.25 mmol) and then acetic acid (99 μl, 1.73 mmol) were added to a suspension of 4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-amine (400 mg, 1.73 mmol) and 8-benzyl-8-azabicyclo[3.2.1]octan-3-one (410 mg, 1.90 mmol) in 1,2-dichloroethane (5 ml), and the resulting mixture was stirred at room temperature for 1 day. The reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate solution and then extracted 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. The residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=100/2) to obtain N-(8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)-4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-amine (283 mg, 38%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract solution was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=100/2)

Sources & evidence

ORD record
ord-b5bef1edfa694a268f70f6587b22d54d
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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