1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66571156, compound

HRID 83612

Reaction equation

HRID 83612 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](O)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[C:59]1([CH3:67])[CH:64]=[CH:63][CH:62]=[C:61]([CH2:65][NH2:66])[CH:60]=1>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:66][CH2:65][C:61]3[CH:62]=[CH:63][CH:64]=[C:59]([CH3:67])[CH:60]=3)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 660153-MethylbenzylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Product 1

HCID 66571156HCID 66571156, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (393 mg, 0.990 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (237 mg, 1.23 mmol), and 1-Hydroxybenzotriazole (167 mg, 1.23 mmol) were dissolved in 2.0 mL of DCM. The reaction was allowed to stir for 10 minutes before N,N-Diisopropylethylamine (216 μL, 1.059 mmol) and m-tolylmethanamine (100 mg, 0.83 mmol) were added as a 1.0 mL DCM solution. The reaction was allowed to stir overnight. The reaction was diluted with water and ethyl acetate. The layers were separated and the organic layer was washed with another aliquot of water. The ethyl acetate layer was washed with 1N HCl followed by saturated sodium bicarbonate then saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude material was triturated with methanol and filtered under vacuum to obtain pure product as a white solid. Yield: 190 mg (White solid)

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with another aliquot of water
  3. washThe ethyl acetate layer was washed with 1N HCl
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was triturated with methanol
  8. filtrationfiltered under vacuum
  9. customto obtain pure product as a white solid

Sources & evidence

ORD record
ord-b96131a290f64217999e9a99eedd08a9
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Linked notes

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