1,2-Dichloroethane → 2-(4-{1-Benzyl-4-[(3-bromo-benzyl)-methyl-amino]-pyrrolidine-2-carbonyl}-piperazin-1-yl)-benzonitrile

HRID 490657Notes

Reaction equation

HRID 490657 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([N:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[CH:17]=2)[CH3:14])[CH2:10][CH:9]1[C:23]([OH:25])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[N:40]1([C:46]2[CH:53]=[CH:52][CH:51]=[CH:50][C:47]=2[C:48]#[N:49])[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.CCN(CC)CC>CN(C=O)C>[CH2:1]([N:8]1[CH2:12][CH:11]([N:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[CH:17]=2)[CH3:14])[CH2:10][CH:9]1[C:23]([N:43]1[CH2:42][CH2:41][N:40]([C:46]2[CH:53]=[CH:52][CH:51]=[CH:50][C:47]=2[C:48]#[N:49])[CH2:45][CH2:44]1)=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2735875N-(2-Cyanophenyl)piperazineHCID 675479001-Benzyl-4-[(3-bromo-benzyl)-methyl-amino]-pyrrolidine-2-carboxylic acid

Product 1

HCID 675469412-(4-{1-Benzyl-4-[(3-bromo-benzyl)-methyl-amino]-pyrrolidine-2-carbonyl}-piperazin-1-yl)-benzonitrileYield 15.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring mixture of 1-benzyl-4-[(3-bromo-benzyl)-methyl-amino]-pyrrolidine-2-carboxylic acid (0.2 mmol), EDC (0.3 mmol) and HOBT (0.3 mmol) in 3 mL of dry DMF were added 2-piperazin-1-yl-benzonitrile (0.24 mmol) and NEt3 (0.6 mmol), and the reaction mixture was stirred overnight and subsequently subjected to preparative HPLC purification on reversed phase eluting with a acetonitrile/water (0.05% NEt3) gradient. 17.5 mg of title product was obtained in 15.2% yield as brown oil.

Workup

  1. customsubsequently subjected to preparative HPLC purification on reversed phase
  2. washeluting with a acetonitrile/water (0.05% NEt3) gradient

Sources & evidence

ORD record
ord-8c79c00498c349338e837b9dc23e350a
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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