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 323480Notes

Reaction equation

HRID 323480 reaction equation
[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]

Participants

8

Reactant 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

Product 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

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fa9e67a13b39459da957521568c24537
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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