Triethylamine → 1-(2-Methoxy-5-(5-methylsulfonyl-1H-tetrazol-1-yl)benzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl)ethyl)-3-phenylpyrrolidine

HRID 637166Notes

Reaction equation

HRID 637166 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:26]([N:29]2[C:33]([S:34]([CH3:37])(=[O:36])=[O:35])=[N:32][N:31]=[N:30]2)=[CH:25][C:4]=1[C:5]([N:7]1[CH2:11][CH2:10][C:9]([CH2:18][CH2:19]OS(C)(=O)=O)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8]1)=[O:6].C(N(CC)CC)C.I.[CH2:46]([O:48][CH2:49][CH2:50][N:51]1[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][C:54]=2[N:53]=[C:52]1[N:60]1[CH2:66][CH2:65][CH2:64][NH:63][CH2:62][CH2:61]1)[CH3:47].CO.ClCCl>C(#N)C.ClCCl>[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:26]([N:29]2[C:33]([S:34]([CH3:37])(=[O:35])=[O:36])=[N:32][N:31]=[N:30]2)=[CH:25][C:4]=1[C:5]([N:7]1[CH2:11][CH2:10][C:9]([CH2:18][CH2:19][N:63]2[CH2:64][CH2:65][CH2:66][N:60]([C:52]3[N:51]([CH2:50][CH2:49][O:48][CH2:46][CH3:47])[C:55]4[CH:56]=[CH:57][CH:58]=[CH:59][C:54]=4[N:53]=3)[CH2:61][CH2:62]2)([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:8]1)=[O:6]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 184647791-(2-methoxy-5-(5-methylsulfonyl-1H-tetrazol-1-yl)benzoyl)-3-(2-methanesulfonyloxyethyl)-3-phenylpyrrolidineHCID 21226129Dichloromethane methanolHCID 865838874-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl) [1,4]diazepane hydriodic acid salt

Product 1

HCID 184645741-(2-Methoxy-5-(5-methylsulfonyl-1H-tetrazol-1-yl)benzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl)ethyl)-3-phenylpyrrolidine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Combine 1-(2-methoxy-5-(5-methylsulfonyl-1H-tetrazol-1-yl)benzoyl)-3-(2-methanesulfonyloxyethyl)-3-phenylpyrrolidine (0.44 g, 0.81 mmol), triethylamine (0.33 g, 3.23 mmol), and 4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt (0.44 g, 8.1 mmol) in acetonitrile (10 mL). Heat to reflux. After 12 hours, cool the reaction mixture, dilute with dichloromethane, and extract with water. Dry the organic layer over MgSO4, filter, and evaporate in uacuo to give a residue. Chromatograph the residue on silica gel eluting with 5% methanol/dichloromethane to give the title compound.

Workup

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

Sources & evidence

ORD record
ord-74d2eab64a914b2e822ffa1f1b3441c1
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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