Methylamine → 3-[4-(4-Ethoxy-phenylethynyl)-phenyl]-N-methyl-propionamide

HRID 330839Notes

Reaction equation

HRID 330839 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([OH:22])=O)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH3:2].[CH3:23][N:24](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN.C(=O)([O-])O.[K+]>CN(C=O)C.O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([NH:24][CH3:23])=[O:22])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 516893Potassium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 666914263-[4-(4-Ethoxy-phenylethynyl)-phenyl]-propionic acid

Product 1

HCID 681811123-[4-(4-Ethoxy-phenylethynyl)-phenyl]-N-methyl-propionamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 100 mg (0.34 mmol) 3-[4-(4-ethoxy-phenylethynyl)-phenyl]-propionic acid (XIV.1) in 5 mL DMF are added 0.12 mL (0.85 mmol) TEA and 0.12 g (0.37 mmol) TBTU and the mixture is stirred for 5 min at rt. After that time, 21 mg (0.68 mmol) methylamine are added and the mixture is stirred at rt for 2 h. Subsequently saturated potassium hydrogencarbonate solution and water are added. The precipitate is filtered, washed with water and dried at 45° C.

Workup

  1. stirringthe mixture is stirred at rt for 2 h
  2. filtrationThe precipitate is filtered
  3. washwashed with water
  4. customdried at 45° C.

Sources & evidence

ORD record
ord-d73f6aeda0044a628dec0f1921554c86
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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