1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59318122, compound

HRID 2190569Notes

Reaction equation

HRID 2190569 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-])=O)[CH:10]=2)[CH:5]=[CH:4]1)[CH3:2].[CH2:15]([O:17][C:18]([CH:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32](O)=[O:33])=[CH:28][CH:27]=2)[CH2:22][CH2:21]1)=[O:19])[CH3:16].CCN=C=NCCCN(C)C>CCO.[Pd]>[CH2:15]([O:17][C:18]([CH:20]1[CH2:21][CH2:22][N:23]([C:26]2[CH:27]=[CH:28][C:29]([C:32](=[O:33])[NH:12][C:9]3[CH:10]=[C:11]4[C:6]([CH:5]=[CH:4][N:3]4[CH2:1][CH3:2])=[CH:7][CH:8]=3)=[CH:30][CH:31]=2)[CH2:24][CH2:25]1)=[O:19])[CH3:16]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 120793201-ethyl-6-nitro-1H-indoleHCID 190638644-[4-(Ethoxycarbonyl)piperidin-1-YL]benzoic acid

Product 1

HCID 59318122HCID 59318122, compoundYield 34.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A slurry of 1-ethyl-6-nitro-1H-indole (100 mg, 0.52 mmol) and 10% Pd/C (21 mg) in EtOH was hydrogenated under 1 atm of H2 for 2 h. The mixture was filtered and concentrated and the intermediate amine was dissolved in CH2Cl2 (5 mL) and treated with 1-(4-carboxy-phenyl)-piperidine-4-carboxylic acid ethyl ester (110 mg, 0.39 mmol) and EDCI (228 mg, 1.19 mmol). After stirring overnight the reaction mixture was partitioned between EtOAc and water. The EtOAc layer was collected, filtered and concentrated. The residue was chromatographed with 20-60% EtOAc in hexanes to afford the product (57 mg, Yield: 34%). HRMS m/z calcd for C25H29N3O3 [M+H]+: 420.2282. Found: 420.2280.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. dissolutionthe intermediate amine was dissolved in CH2Cl2 (5 mL)
  4. customwas partitioned between EtOAc and water
  5. customThe EtOAc layer was collected
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed with 20-60% EtOAc in hexanes

Sources & evidence

ORD record
ord-2c173daa8d874489bb6dbddfdea43157
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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