Diethylamine → HCID 86754765, compound

HRID 1602115Notes

Reaction equation

HRID 1602115 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1/[CH:10]=[CH:11]/[CH:12]=[C:13](\[O:17][CH3:18])/[C:14]([OH:16])=O.[CH2:19]([NH:21][CH2:22][CH3:23])[CH3:20].ON1C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.C1COCC1>[CH2:19]([N:21]([CH2:22][CH3:23])[C:14](=[O:16])/[C:13](/[O:17][CH3:18])=[CH:12]/[CH:11]=[CH:10]/[C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:20]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 19610387HCID 19610387, compound

Product 1

HCID 86754765HCID 86754765, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution of (2Z,4E)-5-(2-indolyl)-2-methoxy-2,4-pentadienoic acid (0.1 g, 0.41 mmol), diethylamine (0.042 ml, 0.41 mmol) and 1-hydroxybenzotriazole (55 mg, 0.41 nmol) in DMF/THF 1:1 (50 Ml), DCC (0.093 g, 0.45 mmol) was added at 0° C. The resulting solution was stirred at room temperature for 48 hours. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane, washed successively with 10% HCl, saturated solution of NaHCO3 and water, dried and evaporated under vacuum. The crude material was purified by column chromatography (EtOAc/hexane 4:6) and triturated with isopropyl ether to yield 21 mg (17.2%) of the title compound as a light yellow solid, m.p.=141-143° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed successively with 10% HCl, saturated solution of NaHCO3 and water
  4. customdried
  5. customevaporated under vacuum
  6. customThe crude material was purified by column chromatography (EtOAc/hexane 4:6)
  7. customtriturated with isopropyl ether

Sources & evidence

ORD record
ord-32c3e5ea66134eafaad48437a75988f6
Source dataset
uspto-grants-1999_11
Patent number
US05981525

Reaction notes

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