Methyl iodide → HCID 21715697, compound

HRID 1277227Notes

Reaction equation

HRID 1277227 reaction equation
[CH3:1][N:2]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:34])/[CH:18]=[CH:19]/[C:20]2[S:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([CH:31]([CH3:33])[CH3:32])=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)=[CH:12][CH:11]=1)[CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[CH3:35][I:36]>CN(C=O)C>[I-:36].[CH3:1][N+:2]([CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)([CH3:35])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:34])/[CH:18]=[CH:19]/[C:20]2[S:21][C:22]([C:25]3[CH:26]=[CH:27][C:28]([CH:31]([CH3:32])[CH3:33])=[CH:29][CH:30]=3)=[CH:23][CH:24]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 18472312HCID 18472312, compound

Product 1

HCID 21715697HCID 21715697, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-3-[5-(4-isopropylphenyl)thiophen-2-yl]acrylamide (80 mg) in DMF (5 ml) was added at room temperature methyl iodide (0.04 ml), and the mixture was stirred for 3 days. Under reduced pressure, the solvent was evaporated, 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-isopropylphenyl)thiophen-2-yl]-2-propenoyl]amino]benzyl]-4-tetrahydropyranyl ammonium iodide (Compound 280) (76.9 mg).

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. additionto the residue was added acetonitrile
  3. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-21c68d72da2043608f3112248acc71f0
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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