1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86673396, compound

HRID 1023365Notes

Reaction equation

HRID 1023365 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12](/[CH:16]=[CH:17]/[C:18]([OH:20])=O)=[CH:11][C:10]=2[CH3:21])=[N:6][CH:7]=1.Cl.[Cl:23][C:24]1[CH:45]=[CH:44][C:27]([O:28][CH2:29][CH2:30][C:31]2[CH:43]=[CH:42][C:34]([CH2:35][N:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)=[CH:33][CH:32]=2)=[CH:26][CH:25]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>O.CCN(CC)CC.CN(C=O)C>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([O:28][CH2:29][CH2:30][C:31]2[CH:43]=[CH:42][C:34]([CH2:35][N:36]3[CH2:37][CH2:38][N:39]([C:18](=[O:20])/[CH:17]=[CH:16]/[C:12]4[CH:11]=[C:10]([CH3:21])[C:9]([O:8][C:5]5[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][N:6]=5)=[C:14]([CH3:15])[CH:13]=4)[CH2:40][CH2:41]3)=[CH:33][CH:32]=2)=[CH:44][CH:45]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 67353520HCID 67353520, compoundHCID 86673397HCID 86673397, compound

Product 1

HCID 86673396HCID 86673396, compoundYield 94.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a DMF (26 mL) solution of (E)-3-{4-[(5-hydroxypyridin-2-yl)oxy]-3,5-dimethylphenyl}prop-2-enoic acid (1.300 g) and 1-{4-[2-(4-chlorophenoxy)ethyl]benzyl}-piperazine hydrochloride (2.116 g) were added HOBT (0.070 g), WSC (1.310 g), and Et3N (1.905 mL) at room temperature, then the resultant mixture was stirred at room temperature over night. The mixture was poured into water, and extracted with AcOEt. The organic layer was washed with water and saturated aqueous NaCl, dried over anhydrous Na2SO4, and evaporated. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1 to 1/0 and then AcOEt/MeOH=4/1) to afford (E)-1-(4-{4-[2-(4-chlorophenoxy)ethyl]benzyl}piperazin-1-yl)-3-{4-[(5-hydroxypyridin-2-yl)oxy]-3,5-dimethylphenyl}prop-2-en-1-one as a pale yellow amorphous powder (2.57 g).

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with water and saturated aqueous NaCl
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1 to 1/0

Sources & evidence

ORD record
ord-20f6022a685a473a84441645ff35c4ed
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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