Methyl iodide → HCID 18472456, compound

HRID 1277226Notes

Reaction equation

HRID 1277226 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11](/[CH:13]=[CH:14]/[C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]([CH3:32])[CH:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[CH:20][CH:19]=3)=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:33][I:34]>CN(C=O)C>[I-:34].[CH3:32][N+:25]([CH:26]1[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1)([CH3:33])[CH2:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:15](=[O:16])/[CH:14]=[CH:13]/[C:11]2[S:12][C:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 18472201HCID 18472201, compound

Product 1

HCID 18472456HCID 18472456, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-3-[5-(4-methylphenyl)thiophen-2-yl]-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]acrylamide (100 mg) in DMF (3 ml) was added at room temperature methyl iodide (0.5 ml), and the mixture was stirred for 2 days. Under reduced pressure, the mixture was concentrated, and to the residue was added acetonitrile. The resulting crystals were collected by filtration to give yellow crystals of N,N-dimethyl-N-[4-[[(E)-3-[5-(4-methylphenyl)thiophen-2-yl]-2-propenoyl]amino]benzyl]-4-tetrahydropyranyl ammonium iodide (Compound 279) (101.1 mg).

Workup

  1. concentrationUnder reduced pressure, the mixture was concentrated
  2. additionto the residue was added acetonitrile
  3. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-395ba2485d3d46f69188bdd2f4bca1a7
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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