Dichloromethane → HCID 10234086, compound

HRID 2269863Notes

Reaction equation

HRID 2269863 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:38]=[C:39]([O:43][CH3:44])[C:40]=1[O:41][CH3:42])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([C:27]([C:29]3[NH:33][C:32]4[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=4[N:30]=3)=[O:28])[CH2:23][CH2:22]2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9]1)=[O:7].N12CCCN=[C:51]1[CH2:50][CH2:49][CH2:48][CH2:47]C2.[C:56]([O:59][CH2:60]C)(=[O:58])[CH3:57].CO.Cl[CH2:65]Cl>C(#N)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:38]=[C:39]([O:43][CH3:44])[C:40]=1[O:41][CH3:42])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([C:27]([C:29]3[N:30]([CH2:65][C:49]4[CH:48]=[CH:47][C:57]([C:56]([O:59][CH3:60])=[O:58])=[CH:51][CH:50]=4)[C:31]4[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=4[N:33]=3)=[O:28])[CH2:23][CH2:22]2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:9]1)=[O:7]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 101213901-(3,4,5-trimethoxy-benzoyl)-3-[2-[4-[1H-benzoimidazole-2-carbonyl]-piperidin-1-yl]-ethyl]-3-phenyl-pyrrolidineHCID 21584119Ethylacetate methanol

Product 1

HCID 10234086HCID 10234086, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 1-(3,4,5-trimethoxy-benzoyl)-3-[2-[4-[1 H-benzoimidazole-2-carbonyl]-piperidin-1-yl]-ethyl]-3-phenyl-pyrrolidine (1.0 g, 1.69 mmol), methyl (4-bromomethyl)benzoate (1.55 g, 6.76 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (2.06 g, 13.52 mmol) in acetonitrile (20 mL). Heat to reflux. After 72 hours, dilute the reaction mixture with ethyl acetate and extract three times with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution, water, and saturated aqueous sodium chloride solution. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 5/1 ethyl acetate/methanol to give an oil. Combine the oil with dichloromethane and extract with 5% sodium bicarbonate solution. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Dry the residue in vacuo at 82° C. to give the title compound: mp; 92.0-96.0° C.; Rf=0.43 (silica gel, 5/1 ethyl acetate/methanol). Elemental Analysis calculated for C44H48N4O7: C 70.95; H 6.50; N 7.52; Found: C 70.78; H 6.56; N 7.48.

Workup

  1. temperatureHeat to reflux
  2. extractionextract three times with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution, water, and saturated aqueous sodium chloride solution
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customto give a residue
  7. extractionextract with 5% sodium bicarbonate solution
  8. dry with materialDry the organic layer over Na2SO4
  9. filtrationfilter
  10. concentrationconcentrate in vacuo
  11. customto obtain a residue
  12. customDry the residue in vacuo at 82° C.

Sources & evidence

ORD record
ord-c01390cc51174b5088bcc10397f92412
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

Loading…