Acetic Acid → HCID 178491739, compound

HRID 2090818Notes

Reaction equation

HRID 2090818 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:5][C:6]=1[CH:7]=O.C(O)(=O)C.[CH3:19][O:20][C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([S:28]([N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]2[CH2:37][O:38][CH2:39][C:40]([N:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)=[O:41])(=[O:30])=[O:29])=[C:23]([CH3:48])[CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[NH:3][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][C:6]=1[CH2:7][N:45]1[CH2:46][CH2:47][N:42]([C:40](=[O:41])[CH2:39][O:38][CH2:37][CH:32]2[CH2:33][CH2:34][CH2:35][CH2:36][N:31]2[S:28]([C:24]2[C:23]([CH3:48])=[CH:22][C:21]([O:20][CH3:19])=[CH:26][C:25]=2[CH3:27])(=[O:29])=[O:30])[CH2:43][CH2:44]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 59746453HCID 59746453, compoundHCID 178520008HCID 178520008, compound

Product 1

HCID 178491739HCID 178491739, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

4-Chloro-2-phenyl-1H-imidazole-5-carbaldehyde (1.5 eq.) and acetic acid (cat.) were added to a solution of 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)-1-(piperazin-1-yl)ethanone (1 eq.) in dichloromethane (25 ml/mmol). The reaction mixture was stirred for 30 min. at 25° C., then sodium triacetoxyborohydride (4 eq.) was added and stirring was carried out for a further 16 h at 25° C. The mixture was diluted with dichloromethane and washed with saturated bicarbonate solution and saturated sodium chloride solution. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography using 3% methanol in ethyl acetate. Yield: 50%; MS, m/z 630.2 (MH+)

Workup

  1. stirringstirring
  2. waitwas carried out for a further 16 h at 25° C
  3. washwashed with saturated bicarbonate solution and saturated sodium chloride solution
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-5aea436c0ea04d97b16002e347e85ac6
Source dataset
uspto-grants-2013_05
Patent number
US08435978B2

Reaction notes

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