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 2230633Notes

Reaction equation

HRID 2230633 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 vacuo 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 vacuo
  7. customto give a residue

Sources & evidence

ORD record
ord-9570696f352d41d78707f0273b411783
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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