Dimethylformamide → HCID 66571216, compound

HRID 83619Notes

Reaction equation

HRID 83619 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([OH:26])=O)[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.O[N:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=N1.[CH3:39]CN=C=NCCCN(C)C.CN(C=O)C>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([NH:30][CH2:34][CH2:35][C:36]3[CH:39]=[N:32][CH:33]=[CH:38][CH:37]=3)=[O:26])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Product 1

HCID 66571216HCID 66571216, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (300 mg, 0.756 mmol), 1-hydroxybenzotriazole (170 mg, 1.261 mmol), EDCI (242 mg, 1.261 mmol) were dissolved in DCM (Ratio: 4.00, Volume: 4.0 ml). the reaction was allowed to stir at room temperature for 10 minutes before adding Hunig'sBase (0.330 ml, 1.891 mmol) and a DMF (Ratio: 1.000, Volume: 1 ml) solution of 2-(pyridin-3-yl)ethanamine, HCl (100 mg, 0.630 mmol). The reaction was stirred overnight. The reaction was diluted with water and ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, 10% aqeuous citric acid solution, followed by saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered and concentrated. The resulting solid was triturated with ethyl acetate to obtain white solid as a product. 1H-NMR (400 MHz, DMSO-d6) 8.40, 7.88, 7.66-7.57, 7.54, 7.36-7.27, 7.20, 7.16-7.04, 6.71, 5.48, 4.56-3.80, 3.32-3.25, 2.89, 2.73, 2.38-2.27, 1.47

Workup

  1. additionbefore adding Hunig'sBase (0.330 ml, 1.891 mmol)
  2. stirringThe reaction was stirred overnight
  3. washThe organic layer was washed with saturated sodium bicarbonate, 10% aqeuous citric acid solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting solid was triturated with ethyl acetate
  8. customto obtain white solid as a product

Sources & evidence

ORD record
ord-ef3e7af14dc740c6b5085e99c316eb9c
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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