1,2-Dichloroethane → HCID 53889813, compound

HRID 399979Notes

Reaction equation

HRID 399979 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][C:33]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:36](O)=[O:37])[CH2:32][CH2:31]3)[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:45][N:46]([CH3:50])[CH2:47][CH2:48][NH2:49].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>ClCCl>[CH3:45][N:46]([CH3:50])[CH2:47][CH2:48][NH:49][C:36]([C:33]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:32][CH2:31][N:30]([CH2:29][CH2:28][C:9]2([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[CH2:10]2)[CH2:35][CH2:34]1)=[O:37]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 218311351-[2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid

Product 1

HCID 53889813HCID 53889813, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid (0.2566 g, 0.4 mmol), N,N-dimethylethylenediamine (0.05 mL, 0.48 mmol), HOBt (65 mg, 0.48 mmol), EDC (92 mg, 0.48 mmol), DIEA (0.08 mL, 0.48 mmol) were combined in dichloromethane (20 mL). The mixture was stirred for 72 h at ambient temperature. The mixture was extracted with H2O. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to obtain a residue. The residue was chromatographed using a Vydac (25×250 mm) C-18 HPLC column to give the title compound: Rt =28 minutes (gradient elution with CH3CN/H2O(0.1% TFA; flow rate=1.0 ml/min.) 10% CH3CN for 10 minutes, 30% CH3CN for 15 minutes, 40% CH3 CN for 15 minutes, 50% CH3CN for 10 minutes, and then 100% CH3 CN).

Workup

  1. extractionThe mixture was extracted with H2O
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto obtain a residue
  6. customThe residue was chromatographed

Sources & evidence

ORD record
ord-c3aeae85400d45faa69ca77eb50b6dd8
Source dataset
uspto-grants-1998_10
Patent number
US05824690

Reaction notes

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