Triethylamine → 3-(4-Pyrrolidin-1-ylmethylphenyl)propynoic acid-(4'-chlorobiphenyl-4-yl)amide

HRID 735007Notes

Reaction equation

HRID 735007 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]([OH:17])=O)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:15](=[O:17])[C:14]#[C:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)=[CH:12][CH:11]=3)=[CH:27][CH:26]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 86754-Amino-4'-chlorodiphenylHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68819317(4-pyrrolidin-1-ylmethylphenyl)propynoic Acid

Product 1

HCID 578457393-(4-Pyrrolidin-1-ylmethylphenyl)propynoic acid-(4'-chlorobiphenyl-4-yl)amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.3 g (1.30 mmol) of (4-pyrrolidin-1-ylmethylphenyl)propynoic acid, 0.27 g (1.32 mmol) of 4′-chlorobiphenyl-4-ylamine, 0.42 g (1.32 mmol) of TBTU, and 0.18 mL (1.32 mmol) of triethylamine in 30 mL of DMF is stirred for 14 hours at ambient temperature. The reaction mixture is evaporated down and the residue is extracted with water and dichloromethane. The organic phase is dried over sodium sulfate. The purification is carried out by column chromatography on silica gel (eluant: dichloromethane/ethanol (10:1)). Yield: 0.095 g (17.5% of theory); melting point: from 180° C.; C26H23ClN2O (M=414.93); calc.: molecular ion peak (M+H)+: 415/417; found: molecular ion peak (M+H)+: 415/417; Rf value: 0.3 (silica gel, dichloromethane/ethanol (5:1)).

Workup

  1. customThe reaction mixture is evaporated down
  2. extractionthe residue is extracted with water and dichloromethane
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customThe purification
  5. customfrom 180° C.

Sources & evidence

ORD record
ord-4277250092a9472c9ad41287c31d8796
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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