1,2-Dichloroethane → HCID 66571517, compound

HRID 83660Notes

Reaction equation

HRID 83660 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][N:9]=[C:8]2[C:12]([OH:14])=O)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.[CH2:41]([NH:48][C:49]([CH:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)=[O:50])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>O.CN(C=O)C>[CH2:41]([NH:48][C:49]([CH:51]1[CH2:56][CH2:55][N:54]([C:12]([C:8]2[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:16][CH:15]=3)[CH:11]=[CH:10][N:9]=2)=[O:14])[CH2:53][CH2:52]1)=[O:50])[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 16232225N-benzylpiperidine-4-carboxamide hydrochlorideHCID 683797411-[(4-Chlorophenyl)methyl]-1H-imidazole-2-carboxylic acid

Product 1

HCID 66571517HCID 66571517, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The following was added sequentially to DMF: 1-(4-chlorobenzyl)-1H-imidazole-2-carboxylic acid (71 mg, 0.298 mmol), DIPEA (0.16 mL, 0.894 mmol), EDC (69 mg, 0.358 mmol), and HOBT (55 mg, 0.358 mmol). This was allowed to stir at rt for 30 min, at which time N-benzylpiperidine-4-carboxamide hydrochloride (76 mg, 0.298 mmol) was added and stirring continued at rt for 14 h. Addition of water caused precipitation, which was collected over a filter and washed with water and small amount of diethyl ether and EtOAc to give the title compound as a white solid. (Yield: 37 mg, 0.085 mmol, 28%) 1H NMR (400 MHz, CDCl3) 7.34-7.23, 7.13, 7.11, 7.04, 6.93, 5.79-5.65, 5.36, 4.63, 4.43, 3.14, 2.82, 2.42-2.32, 1.95, 1.83, 1.70-1.59

Workup

  1. additionwas added
  2. customprecipitation, which
  3. customwas collected over
  4. filtrationa filter
  5. washwashed with water and small amount of diethyl ether and EtOAc

Sources & evidence

ORD record
ord-2d9fdd34cda945b3a3a9a6598629780d
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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