1,2-Dichloroethane → 3-{3,5-Dimethyl-4-[6-(5-o-tolyl-[1,3,4]oxadiazol-2-yl)-1H-benzoimidazol-2-yl]-phenyl}-2,2-dimethyl-propionic acid

HRID 1513296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1513296
C[O:2][C:3](=[O:37])[C:4]([CH3:36])([CH3:35])[CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:17][C:16]3[CH:18]=[C:19]([C:22]4[O:23][C:24]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[CH3:33])=[N:25][N:26]=4)[CH:20]=[CH:21][C:15]=3[N:14]=2)=[C:8]([CH3:34])[CH:7]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.COC(C(C)(C)CC1C=C(C)C(C2NC3C=C(C(O)=O)C=CC=3N=2)=C(C)C=1)=O.CC1C=CC=CC=1C(NN)=O.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>CN(C=O)C.CCOC(C)=O>[CH3:12][C:10]1[CH:11]=[C:6]([CH2:5][C:4]([CH3:36])([CH3:35])[C:3]([OH:37])=[O:2])[CH:7]=[C:8]([CH3:34])[C:9]=1[C:13]1[NH:17][C:16]2[CH:18]=[C:19]([C:22]3[O:23][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[CH3:33])=[N:25][N:26]=3)[CH:20]=[CH:21][C:15]=2[N:14]=1

Komponenten

9

Edukt 6

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 82110o-ToluohydrazideHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 669664013-{3,5-Dimethyl-4-[6-(5-o-tolyl-[1,3,4]oxadiazol-2-yl)-1H-benzoimidazol-2-yl]-phenyl}-2,2-dimethyl-propionic acid methyl esterHCID 669667662-[4-(2-Methoxycarbonyl-2-methyl-propyl)-2,6-dimethyl-phenyl]-3H-benzoimidazole-5-carboxylic acid

Produkt 1

HCID 252354593-{3,5-Dimethyl-4-[6-(5-o-tolyl-[1,3,4]oxadiazol-2-yl)-1H-benzoimidazol-2-yl]-phenyl}-2,2-dimethyl-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

3-{3,5-Dimethyl-4-[6-(5-o-tolyl-[1,3,4]oxadiazol-2-yl)-1H-benzoimidazol-2-yl]-phenyl}-2,2-dimethyl-propionic acid methyl ester. Add EDC (380 mg, 1.98 mmol) and HOBt (268 mg, 1.98 mmol) to a stirring solution of 2-[4-(2-methoxycarbonyl-2-methyl-propyl)-2,6-dimethyl-phenyl]-3H-benzoimidazole-5-carboxylic acid (626 mg, 1.65 mmol) and 2-methyl-benzoic acid hydrazide (248 mg, 1.65 mmol) in DMF (6 mL) under N2. Upon disappearance of the carboxylic acid by LC/MS, dilute the reaction with EtOAc (60 mL) and extract with water (20 mL) followed by brine (10 mL). Dry the organic phase over Na2SO4 and evaporate the solvent. Dissolve the residue in DMF (6 mL) and add Burgess reagent (1.18 g, 4.95 mmol). Heat the mixture my microwave irradiation to 150° C. for 15 min. Dilute the reaction with EtOAc (100 mL) and extract with water (25 mL). Extract the organic phase with saturated NaHCO3 (2×25 mL) followed by brine (20 mL). Dry the organic phase over Na2SO4 and evaporate the solvent. Purify the residue by silica gel chromatography (10-45% ACN/DCM) to afford the title compound as a yellow oil: (M+H)+495.3.

Aufarbeitung

  1. extractionextract with water (20 mL)
  2. dry with materialDry the organic phase over Na2SO4
  3. customevaporate the solvent
  4. dissolutionDissolve the residue in DMF (6 mL)
  5. temperatureHeat
  6. customthe mixture my microwave irradiation to 150° C. for 15 min
  7. additionDilute
  8. extractionextract with water (25 mL)
  9. extractionExtract the organic phase with saturated NaHCO3 (2×25 mL)
  10. dry with materialDry the organic phase over Na2SO4
  11. customevaporate the solvent
  12. customPurify the residue by silica gel chromatography (10-45% ACN/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-7dab397467b44dc2ac24497d62bd6c4b
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217065B2

Notizen zur Reaktion

Wird geladen…