Acetic Acid → HCID 69433732, compound

HRID 1269976Notes

Reaction equation

HRID 1269976 reaction equation
[CH3:1][C:2]1[C:10]([O:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][C@H:14]([NH2:18])[CH2:13]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O.C(O)(=O)C.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO>[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][NH:18][C@H:14]1[CH2:15][CH2:16][CH2:17][C@@H:12]([O:11][C:10]2[C:2]([CH3:1])=[C:3]3[C:7](=[CH:8][CH:9]=2)[NH:6][N:5]=[CH:4]3)[CH2:13]1

Participants

7

Reactant 5

HCID 176Acetic Acid2×HCID 69962-ChlorobenzaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 69431191HCID 69431191, compound

Product 1

HCID 69433732HCID 69433732, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the cis-3-[(4-methyl-1H-indazol-5-yl) oxy]cyclohexanamine (100 mg, 0.407 mmol) obtained in Example 411 in methanol (5 ml) were added 2-chlorobenzaldehyde (46 μl, 0.407 mmol) and acetic acid (23 μl, 0.407 mmol), and the resulting mixture was stirred at room temperature for 30 minutes. Then, acetic acid (46 μl, 0.814 mmol) and sodium cyanoborohydride (28 mg, 0.447 mmol) were added thereto and stirred for 2 hours and a half. Subsequently, the reaction solution was poured into a saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=30/1) to obtain cis-N-(2-chlorobenzyl)-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexanamine (100 mg, 66%).

Workup

  1. stirringstirred for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-49abba02c6034768932b93470c23a469
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

Loading…