1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 10478659, compound

HRID 1991077Notes

Reaction equation

HRID 1991077 reaction equation
C([C@H]1NC[CH2:6][N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH2:4]1)C.CCN=C=N[CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26].C1C=CC2N([OH:37])N=NC=2C=1.[Cl:38][C:39]1[CH:44]=[CH:43][C:42]([C:45](=C)[C:46](O)=O)=[C:41]([NH:50][C:51]([NH2:53])=[O:52])[CH:40]=1>C(Cl)Cl>[Cl:38][C:39]1[CH:44]=[CH:43][C:42](/[CH:45]=[CH:46]/[C:27]([N:25]2[CH2:26][CH2:4][N:5]([CH2:9][C:10]3[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=3)[CH2:6][C@H:24]2[CH2:23][CH3:22])=[O:37])=[C:41]([NH:50][C:51]([NH2:53])=[O:52])[CH:40]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 45095470HCID 45095470, compoundHCID 86606867HCID 86606867, compound

Product 1

HCID 10478659HCID 10478659, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-3-Ethyl-1-(4-fluorobenzyl)-piperazine (88.8 mg, 0.4 mmol), EDCI (152 mg, 0.8 mmol), HOBT (110 mg, 0.8 mmol) and (E)-3-(4-Chloro-2-ureido-phenyl-acrylic acid (96 mg, 0.4 mmol) were dissolved in 5 ml DCM and this mixture was stirred at room temperature over night. The mixture was diluted with 50 ml DCM and extracted 3 times with water and once with saturated sodium chloride solution. The title compound was purified by chromatography (SiO2, ethyl acetate/MeOH/NH3conc, 98/2/0.2) and was isolated as pale solid (60 mg, 34%)

Workup

  1. extractionextracted 3 times with water
  2. customThe title compound was purified by chromatography (SiO2, ethyl acetate/MeOH/NH3conc, 98/2/0.2)

Sources & evidence

ORD record
ord-02b5036b9105437e8432fe9d10050514
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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