1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 9980976, compound

HRID 1991080Notes

Reaction equation

HRID 1991080 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1/[CH:12]=[CH:13]/[C:14]([OH:16])=O)(=[O:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[F:38][C:39]1[CH:53]=[CH:52][C:42]([CH2:43][N:44]2[CH2:49][CH2:48][NH:47][C@H:46]([CH2:50][OH:51])[CH2:45]2)=[CH:41][CH:40]=1>C1COCC1>[Cl:11][C:9]1[CH:8]=[CH:7][C:6](/[CH:12]=[CH:13]/[C:14]([N:47]2[CH2:48][CH2:49][N:44]([CH2:43][C:42]3[CH:41]=[CH:40][C:39]([F:38])=[CH:53][CH:52]=3)[CH2:45][C@H:46]2[CH2:50][OH:51])=[O:16])=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 58683694HCID 58683694, compoundHCID 68538268HCID 68538268, compound

Product 1

HCID 9980976HCID 9980976, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-3-(2-Acetylamino-4-chloro-phenyl)-acrylic acid (2.2 g, 9.36 mmol), EDCI (3.6 g, 18.7 mmol); HOBT (2.5 g, 18.7 mmol) and 2.1 g (9.36 mmol) [(S)-4-(4-Fluorobenzyl)-piperazin-2-yl]-methanol were dissolved in 200 ml THF and stirred for 20 hours at room temperature. This mixture was then extracted 3 times with water and once with saturated sodium chloride solution. The title compound was purified by chromatography (SiO2, ethyl acetate/MeOH/NH3conc. 90/10/1) and was isolated as a pale solid (1.6 g, 39%)

Workup

  1. extractionThis mixture was then extracted 3 times with water
  2. customThe title compound was purified by chromatography (SiO2, ethyl acetate/MeOH/NH3conc. 90/10/1)

Sources & evidence

ORD record
ord-d65a3c6b0473432d920f33db20d49184
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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