Water → HCID 54483006, compound

HRID 366525Notes

Reaction equation

HRID 366525 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CC[N:15]=C=NCCCN(C)C.[CH2:24]([CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:24]([CH:31]1[CH2:36][CH2:35][N:34]([C:2]2[NH:1][C:9]3[C:4]([CH:3]=2)=[CH:5][C:6]([C:10]([NH2:15])=[O:12])=[CH:7][CH:8]=3)[CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 317384-BenzylpiperidineHCID 742801H-Indole-5-Carboxylic Acid

Product 1

HCID 54483006HCID 54483006, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Indole-5-carboxylic acid (1.61 g, 10 mMol) was reacted with EDAC (1.92 g, 10 mMol) in 40 mL dry DMF for 15 minutes. 4-Benzylpiperidine (1.75 g, 10 mMol) was added followed by DMAP (20 mg, catalyst) and the reaction mixture was stirred for 20 h. The mixture was poured into water and extracted with methylene chloride (3×100 mL). The combined extract was washed with dilute hydrochloric acid, saturated sodium bicarbonate and water and dried over MgSO4. After evaporation of the solvent, the residue was chromatographed with methylene chloride-methanol (0 to 2% methanol, gradient) to yield 1.60 g (50%) of the product after recrystallization from ether-Hexane. MS (ESI) m/e 318 (M+), (317+ --H). 1HNMR (CDCl3)δ=8.5 (s, 1H); 7.7 (s, 1H), 7.4-7.15 (m, 8H); 6.8 (s, 1H); 4.8-4.6 (br, m, 1H); 4.1-3.9 9br, m, 1H); 3.1-2.7 (br, m, 2H); 2.6 (d, 2H); 1.9-1.7 (br, m, 3H); 1.4-1,2 (br, m, 2H).

Workup

  1. extractionextracted with methylene chloride (3×100 mL)
  2. extractionThe combined extract
  3. washwas washed with dilute hydrochloric acid, saturated sodium bicarbonate and water
  4. dry with materialdried over MgSO4
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed with methylene chloride-methanol (0 to 2% methanol, gradient)

Sources & evidence

ORD record
ord-69c28f89650e4d2487b216f193dbfdf1
Source dataset
uspto-grants-2000_10
Patent number
US06130235

Reaction notes

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