1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57385795, compound

HRID 83625Notes

Reaction equation

HRID 83625 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.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.[N:50]1[CH:55]=[CH:54][CH:53]=[C:52]([CH2:56][NH2:57])[CH:51]=1>C(Cl)Cl>[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:57][CH2:56][C:52]3[CH:51]=[N:50][CH:55]=[CH:54][CH:53]=3)=[O:26])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 310183-PyridinemethanamineHCID 757711-HydroxybenzotriazoleHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Product 1

HCID 57385795HCID 57385795, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (365 mg, 0.920 mmol), 1-hydroxybenzotriazole (249 mg, 1.839 mmol) and EDCI (353 mg, 1.839 mmol) were dissolved in DCM (Volume: 3.0 ml). The suspension was stirred at room temperature for 10 minutes where it turned clear. Hunig'sBase (0.321 ml, 1.839 mmol) and pyridin-3-ylmethanamine (199 mg, 1.839 mmol) were added. The reaction was stirred at room temperature overnight. Solid precipitate formed overnight. The reaction was concentrated and triturated with ethyl acetate to afford product as a white solid. (Yield: 315 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 8.46, 8.40, 7.70-7.60, 7.54, 7.40-7.29, 7.21, 7.13-7.05, 6.73, 5.49, 4.38, 4.30, 4.04, 2.95, 2.47-2.39, 1.71, 1.42

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. customSolid precipitate formed overnight
  3. concentrationThe reaction was concentrated
  4. customtriturated with ethyl acetate
  5. customto afford product as a white solid

Sources & evidence

ORD record
ord-c3201cbbc44d4cb2ba6131a3a5aeb013
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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