1,2-Dichloroethane → 1-(1-(4-chlorobenzyl)-1H-benzo[d]imidazole-2-carbonyl)-N-(2-(pyridin-4-yl)ethyl)piperidine-4-carboxamide

HRID 83653

Reaction equation

HRID 83653 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24](O)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.C(Cl)CCl.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[N:52]1[CH:57]=[CH:56][C:55]([CH2:58][CH2:59][NH2:60])=[CH:54][CH:53]=1>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([NH:60][CH2:59][CH2:58][C:55]3[CH:56]=[CH:57][N:52]=[CH:53][CH:54]=3)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:27][CH:28]=1

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 832754-PyridineethanamineHCID 68380045HCID 68380045, compound

Product 1

HCID 665715191-(1-(4-chlorobenzyl)-1H-benzo[d]imidazole-2-carbonyl)-N-(2-(pyridin-4-yl)ethyl)piperidine-4-carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(1-(4-chlorobenzyl)-1H-benzo[d]imidazole-2-carbonyl)piperidine-4-carboxylic acid (50 mg, 0.126 mmol), EDC (48.2 mg, 0.251 mmol), and 1-hydroxybenzotriazole (34.0 mg, 0.251 mmol) were dissolved in DCM (Volume: 2.0 mL). The reaction was allowed to stir for 10 minutes before the addition of Hunig's Base (0.044 mL, 0.251 mmol) and 2-(pyridin-4-yl)ethanamine (0.030 mL, 0.251 mmol). The reaction was allowed to stir overnight. The reaction was diluted with water and ethyl acetate. The organic layer was washed with saturated sodium bicarbonate and saturated sodium chloride. The ethyl acetate layer was dried over magnesium sulfate, filtered and concentrated. The crude material was triturated in diethyl ether/ethyl acetate to obtain white solid. 1H-NMR (500 MHz, DMSO-d6) 8.47-8.43, 7.93, 7.74, 7.61, 7.39, 7.35-7.24, 7.21, 5.55, 4.45, 3.98, 3.33-3.28, 3.04, 2.87, 2.73, 2.40-2.31, 1.74, 1.58-1.32

Workup

  1. washThe organic layer was washed with saturated sodium bicarbonate and saturated sodium chloride
  2. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was triturated in diethyl ether/ethyl acetate
  6. customto obtain white solid

Sources & evidence

ORD record
ord-9b19dee1017449189f94044d46d2e729
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Linked notes

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