Cyclohexanone → HCID 11754457, compound

HRID 1296355Notes

Reaction equation

HRID 1296355 reaction equation
C(N(CC)CC)C.Cl.[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[C:20]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[C:19]([CH3:28])[C:18]([CH:29]2[O:34][CH2:33][CH2:32][NH:31][CH2:30]2)=[N:17]1.[C:35]1(=O)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([C:20]2[N:16]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[Cl:9])[N:17]=[C:18]([CH:29]3[O:34][CH2:33][CH2:32][N:31]([CH:35]4[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]4)[CH2:30]3)[C:19]=2[CH3:28])=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 7967CyclohexanoneHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 69416303HCID 69416303, compound

Product 1

HCID 11754457HCID 11754457, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

Triethyl amine (37 μl, 0.27 mmol) was added into the solution of 2-[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-1H-pyrazol-3-yl]-morpholine hydrochloride 5A-2 (75 mg, 0.18 mmol) and cyclohexanone (18 μl, 0.18 mmol) in 0.5 ml 1,2-dichloroethane. The reaction mixture was then treated with sodium triacetoxyborohydride (52 mg, 0.25 mmol) followed by acetic acid at room temperature. Upon the completion of the reaction, the reaction mixture was partitioned with ethyl acetate and saturated NaHCO3. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by chromatography (silica, 60% ethyl acetate/hexanes) to give the title compound 5A-3 as a white solid (40 mg).

Workup

  1. customUpon the completion of the reaction
  2. customthe reaction mixture was partitioned with ethyl acetate and saturated NaHCO3
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (silica, 60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-452a259f44cb4473b2e4889a59d019e7
Source dataset
uspto-grants-2007_07
Patent number
US07247628B2

Reaction notes

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