Diisopropylethylamine → 1-(2-Methoxy-5-(1H-triazol-1-ylmethyl)benzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl)ethyl)-3-phenylpyrrolidine

HRID 2230616Notes

Reaction equation

HRID 2230616 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[N:15]1[CH2:21][CH2:20][CH2:19][N:18]([CH2:22][CH2:23][C:24]2([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:28][CH2:27][NH:26][CH2:25]2)[CH2:17][CH2:16]1)[CH3:2].C(N(CC)C(C)C)(C)C.[CH3:44][O:45][C:46]1[CH:54]=[CH:53][C:52]([CH2:55][N:56]2[CH:60]=[CH:59][N:58]=[N:57]2)=[CH:51][C:47]=1[C:48](Cl)=[O:49].CO.ClCCl>O1CCCC1.C(OCC)(=O)C>[CH3:44][O:45][C:46]1[CH:54]=[CH:53][C:52]([CH2:55][N:56]2[CH:60]=[CH:59][N:58]=[N:57]2)=[CH:51][C:47]=1[C:48]([N:26]1[CH2:27][CH2:28][C:24]([CH2:23][CH2:22][N:18]2[CH2:19][CH2:20][CH2:21][N:15]([C:7]3[N:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[N:8]=3)[CH2:16][CH2:17]2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:25]1)=[O:49]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 184645252-Methoxy-5-(1H-triazol-1-ylmethyl)benzoyl ChlorideHCID 184646773-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl)ethyl)-3-phenylpyrrolidineHCID 21226129Dichloromethane methanol

Product 1

HCID 184646391-(2-Methoxy-5-(1H-triazol-1-ylmethyl)benzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl)ethyl)-3-phenylpyrrolidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl)ethyl)-3-phenylpyrrolidine (0.48 g, 1.04 mmol), N,N-diisopropylethylamine (0.35 mL), and 2-methoxy-5-(1H-triazol-1-ylmethyl)benzoyl chloride (0.22 g, 0.94 mmol) in tetrahydrofuran (50 mL). After 18 hours, dilute the reaction mixture with ethyl acetate and extract with a saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with methanol/dichloromethane/concentrated aqueous ammonia 10/90/0.5 give the title compound: Rf=0.68 (silica gel, methanol/dichloromethane/concentrated aqueous ammonia 10/90/0.1).

Workup

  1. extractionextract with a saturated aqueous sodium bicarbonate solution
  2. dry with materialDry the organic layer over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customto give a residue

Sources & evidence

ORD record
ord-818039d2f89047b2b9f83df450d79706
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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