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 1360800ノート

反応式

HRID 1360800 の反応式
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

参加物

8

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0e46fa10cbeb4d14b01eb98226b2fa08
出典データセット
uspto-grants-2011_02
特許番号
US07879850B2

反応ノート

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