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Diisopropylethylamine → N-[3-(2-Methylaminoethoxy)-4-methoxyphenyl]-2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxamide

HRID 2392683
Notes
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Reaction equation

HRID 2392683 reaction equation
[CH3:1][N:2](C)[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[N:33]=[C:32]([CH3:34])[O:31][N:30]=4)=[CH:25][C:24]=3[CH3:35])=[CH:19][CH:18]=2)=[O:16])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].ClC(OC(Cl)C)=O.C(N(C(C)C)CC)(C)C>ClCCCl>[CH3:1][NH:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH:14][C:15]([C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[N:33]=[C:32]([CH3:34])[O:31][N:30]=4)=[CH:25][C:24]=3[CH3:35])=[CH:21][CH:22]=2)=[O:16])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 3292447SB 216641

Product 1

HCID 18672663N-[3-(2-Methylaminoethoxy)-4-methoxyphenyl]-2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxamideYield 68%

Reagents, catalysts & solvents 1

HCID 111,2-Dichloroethane
Solvent

Procedure

A solution of N-[3-(2-dimethylaminoethoxy)-4-methoxyphenyl]-2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxamide (E1, 0.2 g, 0.41 mmole) in 1,2-dichloroethane (5 ml) was treated at room temperature with 1-chloroethyl chloroformate (0.12 ml, 1.12 mmole) followed by diisopropylethylamine (0.15 ml, 0.86 mmole). The mixture was stirred for 2 hours at room temperature. After removal of solvent in vacuo the residue was treated with methanol (8 ml) and heated under reflux for 30 minutes. The reaction mixture was concentrated in vacuo and the residue treated with saturated aqueous potassium carbonate (10 ml) and extracted with dichloromethane (3×10 ml). The combined organic extracts were dried and concentrated in vacuo. Flash column chromatography on silica gel eluting with 5% MeOH/CH2Cl2 gave the title compound as a light pink solid (0.13 g, 68%) mp 97°-99° C.

Workup

  1. customAfter removal of solvent in vacuo the residue
  2. additionwas treated with methanol (8 ml)
  3. temperatureheated
  4. temperatureunder reflux for 30 minutes
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. additionthe residue treated with saturated aqueous potassium carbonate (10 ml)
  7. extractionextracted with dichloromethane (3×10 ml)
  8. customThe combined organic extracts were dried
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f3d1e8c08a9f4dc5872255e119ad054f
Source dataset
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05801170

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes