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 methyl ester

HRID 1360800노트

반응식

HRID 1360800 반응식
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:15][O:16][C:17]([C:19]([CH3:42])([CH3:41])[CH2:20][C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([C:28]2[NH:29][C:30]3[CH:36]=[C:35]([C:37](O)=[O:38])[CH:34]=[CH:33][C:31]=3[N:32]=2)=[C:23]([CH3:40])[CH:22]=1)=[O:18].[CH3:43][C:44]1[CH:53]=[CH:52][CH:51]=[CH:50][C:45]=1[C:46]([NH:48][NH2:49])=O.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>CN(C=O)C.CCOC(C)=O>[CH3:15][O:16][C:17](=[O:18])[C:19]([CH3:41])([CH3:42])[CH2:20][C:21]1[CH:22]=[C:23]([CH3:40])[C:24]([C:28]2[NH:29][C:30]3[CH:36]=[C:35]([C:37]4[O:38][C:46]([C:45]5[CH:50]=[CH:51][CH:52]=[CH:53][C:44]=5[CH3:43])=[N:48][N:49]=4)[CH:34]=[CH:33][C:31]=3[N:32]=2)=[C:25]([CH3:27])[CH:26]=1

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 82110o-ToluohydrazideHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 669667662-[4-(2-Methoxycarbonyl-2-methyl-propyl)-2,6-dimethyl-phenyl]-3H-benzoimidazole-5-carboxylic acid

생성물 1

HCID 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 ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0e46fa10cbeb4d14b01eb98226b2fa08
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879850B2

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