Acetonitrile → HCID 10123138, compound

HRID 2269849Notes

Reaction equation

HRID 2269849 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:19]2[CH:27]=[CH:26][C:22]3[O:23][CH2:24][O:25][C:21]=3[CH:20]=2)([CH2:13][CH2:14]S(C)(=O)=O)[CH2:9]1)=[O:7].C(N(C(C)C)CC)(C)C.C(#N)C.[F:47][C:48]1[CH:71]=[CH:70][C:51]([CH2:52][N:53]2[C:57]3[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=3[N:55]=[C:54]2[C:62]([CH:64]2[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]2)=[O:63])=[CH:50][CH:49]=1>C(OCC)(=O)C.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:13][CH2:14][N:67]2[CH2:68][CH2:69][CH:64]([C:62]([C:54]3[N:53]([CH2:52][C:51]4[CH:50]=[CH:49][C:48]([F:47])=[CH:71][CH:70]=4)[C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=4[N:55]=3)=[O:63])[CH2:65][CH2:66]2)([C:19]2[CH:27]=[CH:26][C:22]3[O:23][CH2:24][O:25][C:21]=3[CH:20]=2)[CH2:9]1)=[O:7]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 155428834-(1-(4-fluorobenzyl)-1H-benzimidazole-2-carbonyl)piperidineHCID 15542887HCID 15542887, compound

Product 1

HCID 10123138HCID 10123138, compound

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Combine 1-(3,4,5-trimethoxy-benzoyl)-3-(benzo[1,3]dioxol-5-yl)-3-(2-methanesulfonyl-ethyl)-pyrrolidine (0.64 g, 1.26 mmol), diisopropylethylamine (0.33 g, 2.6 mmol), acetonitrile (14 mL), and 4-[1-(4-fluoro-benzyl)-1 H-benzoimidazole-2-carbonyl]-piperidine (0.64 g, 1.9 mmol). Heat to reflux. After 48 hours, partition the reaction mixture between ethyl acetate and water. Extract 2 times with water, a saturated sodium bicarbonate solution, and a saturated sodium chloride solution. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 10/1 ethyl acetate/methanol to give a residue. Partition the residue between dichloromethane and water. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo at 70° C. to give the title compound: Rf=0.54 (silica gel, 10/1 ethyl acetate/methanol); mp; 94-97° C.

Workup

  1. temperatureHeat to reflux
  2. custompartition the reaction mixture between ethyl acetate and water
  3. extractionExtract 2 times with water
  4. dry with materialDry the organic layer over Na2SO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customto give a residue
  8. customPartition the residue between dichloromethane and water
  9. dry with materialDry the organic layer over Na2SO4
  10. filtrationfilter
  11. customevaporate in vacuo at 70° C.

Sources & evidence

ORD record
ord-4bc17a1e30d447afbd05cd514982a662
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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