1-Hydroxybenzotriazole → 3'-{({2-[4-(Aminosulfonyl)phenyl]ethyl}[(E)-3-phenyl-2-propenoyl]amino)methyl}-N-[2-(1-pyrrolidinyl)ethyl][1,1'-biphenyl]-3-carboxamide

HRID 9775

Reaction equation

HRID 9775 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][CH2:14][C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([NH:29][CH2:30][CH2:31][N:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)=[O:28])[CH:22]=3)[CH:18]=[CH:19][CH:20]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:37](O)(=[O:46])/[CH:38]=[CH:39]/[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>ClCCl.CN(C=O)C>[NH2:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][N:13]([CH2:14][C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([NH:29][CH2:30][CH2:31][N:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)=[O:28])[CH:22]=3)[CH:18]=[CH:19][CH:20]=2)[C:37](=[O:46])/[CH:38]=[CH:39]/[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 444539Cinnamic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 102392483'-[{2-[4-(aminosulfonyl)phenyl]ethyl}aminomethyl]-N-[2-(1-pyrrolidinyl)ethyl][1,1'-biphenyl]-3-carboxamide

Product 1

HCID 219869933'-{({2-[4-(Aminosulfonyl)phenyl]ethyl}[(E)-3-phenyl-2-propenoyl]amino)methyl}-N-[2-(1-pyrrolidinyl)ethyl][1,1'-biphenyl]-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

3′-[{2-[4-(Aminosulfonyl)phenyl]ethyl}aminomethyl]-N-[2-(1-pyrrolidinyl)ethyl]-[1,1′-biphenyl]-3-carboxamide (506 mg), trans-cinnamic acid (163 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI.HCl; 211 mg) and 1-hydroxybenzotriazole (HOBT; 149 mg) were dissolved in a mixed solvent of dichloromethane (15 ml) and DMF (7 ml), and the mixture was stirred at room temperature for 18 hours. The solvent was evaporated under reduced pressure, and water was added to the residues which were then extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residues were purified by silica gel column chromatography (dichloromethane/methanol=98/2), whereby the title compound (284 mg) was obtained.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water
  2. additionwas added to the residues which
  3. extractionwere then extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residues were purified by silica gel column chromatography (dichloromethane/methanol=98/2), whereby the title compound (284 mg)
  8. customwas obtained

Sources & evidence

ORD record
ord-b696eafa817c4dfc8a4718f4178b9314
Source dataset
uspto-grants-2006_08
Patent number
US07091247B2

Linked notes

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