Methyl iodide → HCID 18472456, compound

HRID 2228241Notes

Reaction equation

HRID 2228241 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-5ae053be9dee4835bfa91fbd3f89eb85
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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