Triethylamine → 1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-(2-(4-(1-(fur-2-ylmethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine

HRID 323480노트

반응식

HRID 323480 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[CH3:23][O:24][C:25]1[CH:50]=[CH:49][C:48]([N:51]2[CH:55]=[N:54][N:53]=[N:52]2)=[CH:47][C:26]=1[C:27]([N:29]1[CH2:33][CH2:32][C:31]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([CH2:34][CH2:35]OS(C)(=O)=O)[CH2:30]1)=[O:28].C(N(CC)CC)C.C(OCC)(=O)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C.ClCCl>[CH3:23][O:24][C:25]1[CH:50]=[CH:49][C:48]([N:51]2[CH:55]=[N:54][N:53]=[N:52]2)=[CH:47][C:26]=1[C:27]([N:29]1[CH2:33][CH2:32][C:31]([CH2:34][CH2:35][N:20]2[CH2:19][CH2:18][CH:17]([NH:16][C:8]3[N:7]([CH2:6][C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[N:9]=3)[CH2:22][CH2:21]2)([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:30]1)=[O:28]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 135879951-(2-furanylmethyl)-N-(4-piperidinyl)-1H-benzimidazol-2-amineHCID 184648112-methoxy-5-(1H-tetrazol-1-yl)benzoyl-3-phenyl-3-(2-methanesulfonyloxyethyl)-pyrrolidine

생성물 1

HCID 98312321-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-(2-(4-(1-(fur-2-ylmethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

Combine (1-(fur-2-ylmethyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine (0.236 g, 0.8 mmol), 1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine (prepared from (−)-3-(2-hydroxyethyl)-3-phenylpyrrolidine (R,R)-di-p-anisoyltartaric acid salt) (0.38 g, 0.80 mmol), triethylamine (0.133 mL, 7.2 mmol), and tetrabutylammonium iodide (30 mg) in acetonitrile (11.4 mL). Heat to reflux. After 42 hours, cool, dilute the reaction mixture with dichloromethane, and extract with water. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give the title compound.

후처리

  1. temperatureHeat to reflux
  2. temperaturecool
  3. extractionextract with water
  4. dry with materialDry the organic layer over MgSO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customto give a residue

출처 및 근거

ORD 기록
ord-fa9e67a13b39459da957521568c24537
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211199B1

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