Methyl iodide → HCID 18472456, compound

HRID 1387981Notes

Reaction equation

HRID 1387981 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)amino-methyl]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-fa9fa5099d4d4a49882bee8a9fa9acf3
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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