1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58683756, compound

HRID 1991084Notes

Reaction equation

HRID 1991084 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.[CH2:38]([O:45][CH2:46][C@@H:47]1[CH2:52][N:51]([CH2:53][C:54]2[CH:59]=[CH:58][C:57]([F:60])=[CH:56][CH:55]=2)[C@@H:50]([CH3:61])[CH2:49][NH:48]1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C1COCC1>[CH2:38]([O:45][CH2:46][C@@H:47]1[CH2:52][N:51]([CH2:53][C:54]2[CH:55]=[CH:56][C:57]([F:60])=[CH:58][CH:59]=2)[C@@H:50]([CH3:61])[CH2:49][N:48]1[C:14](=[O:16])/[CH:13]=[CH:12]/[C:6]1[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:5]=1[NH:4][C:1](=[O:3])[CH3:2])[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 58683736HCID 58683736, compoundHCID 68538268HCID 68538268, compound

Product 1

HCID 58683756HCID 58683756, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-3-(2-Acetylamino-4-chloro-phenyl)-acrylic acid (168 mg, 0.7 mmol), EDCI (269 mg, 1.4 mmol); HOBT (190 mg, 1.4 mmol) and 230 mg (0.7 mmol) (2S,5S)-5-Benzyloxymethyl-1-(4-fluorobenzyl)-2-methyl-piperazine (prepared as outlined in example 47) were dissolved in 10 ml THF and stirred for 28 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 (180 mg, 47%)

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-4aafd923616a4ab198317d4b60110586
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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