Chlorobenzene → HCID 9832306, compound

HRID 2269857Notes

Reaction equation

HRID 2269857 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:30]=[C:31]([O:36][CH2:37][CH3:38])[C:32]=1[O:33][CH2:34][CH3:35])[C:7]([N:9]1[CH2:13][CH2:12][C:11]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)([CH2:14][CH2:15]S(C)(=O)=O)[CH2:10]1)=[O:8])[CH3:2].C(N(C(C)C)CC)(C)C.ClC1C=CC=CC=1.[F:55][C:56]1[CH:79]=[CH:78][C:59]([CH2:60][N:61]2[C:65]3[CH:66]=[CH:67][CH:68]=[CH:69][C:64]=3[N:63]=[C:62]2[C:70]([CH:72]2[CH2:77][CH2:76][NH:75][CH2:74][CH2:73]2)=[O:71])=[CH:58][CH:57]=1>C(OCC)(=O)C.CO.C(OCC)(=O)C.CCCCCC>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:30]=[C:31]([O:36][CH2:37][CH3:38])[C:32]=1[O:33][CH2:34][CH3:35])[C:7]([N:9]1[CH2:13][CH2:12][C:11]([CH2:14][CH2:15][N:75]2[CH2:76][CH2:77][CH:72]([C:70]([C:62]3[N:61]([CH2:60][C:59]4[CH:58]=[CH:57][C:56]([F:55])=[CH:79][CH:78]=4)[C:65]4[CH:66]=[CH:67][CH:68]=[CH:69][C:64]=4[N:63]=3)=[O:71])[CH2:73][CH2:74]2)([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[CH2:10]1)=[O:8])[CH3:2]

Participants

7

Reactant 4

HCID 7964ChlorobenzeneHCID 81531DiisopropylethylamineHCID 155428834-(1-(4-fluorobenzyl)-1H-benzimidazole-2-carbonyl)piperidineHCID 18333340HCID 18333340, compound

Product 1

HCID 9832306HCID 9832306, compound

Reagents, catalysts & solvents 2

HCID 21226206Ethyl acetate hexaneSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

Combine 1-(3,4,5-triethoxy-benzoyl)-3-(3,4-dimethoxy-phenyl)-3-(2-methanesulfonyl-ethyl)-pyrrolidine (0.31 g, 0.55 mmol), diisopropylethylamine (0.14 g, 1.1 mmol), chlorobenzene (5 mL), and 4-[1-(4-fluoro-benzyl)-1 H-benzoimidazole-2-carbonyl]-piperidine (0.28 g, 0.83 mmol) Heat to 120° C. After 4 hours, partition the reaction mixture between ethyl acetate and water. Extract 2 times with water and a 5% sodium bicarbonate solution. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 3/1 ethyl acetate/hexane and then 10/1/0.1 ethyl acetate/methanol/concentrated aqueous ammonia to give the title compound: Rf=0.60 (silica gel, 10/1/0.1 ethyl acetate/methanol/concentrated aqueous ammonia); mp; 155-160° C.

Workup

  1. custompartition the reaction mixture between ethyl acetate and water
  2. extractionExtract 2 times with water
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customto give a residue

Sources & evidence

ORD record
ord-9ce076a4067f45c2b0248e7e4f7e0fb4
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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