Methyl iodide → HCID 21995814, compound

HRID 1978790Notes

Reaction equation

HRID 1978790 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[S:21](=[O:23])(=[O:22])[CH2:20][CH2:19][C:18]([C:24]([NH:26][C:27]4[CH:32]=[CH:31][C:30]([CH2:33][N:34]([CH3:41])[CH:35]5[CH2:40][CH2:39][O:38][CH2:37][CH2:36]5)=[CH:29][CH:28]=4)=[O:25])=[CH:17][C:16]=3[CH:42]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH3:43][I:44]>CN(C=O)C>[I-:44].[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[S:21](=[O:23])(=[O:22])[CH2:20][CH2:19][C:18]([C:24]([NH:26][C:27]4[CH:28]=[CH:29][C:30]([CH2:33][N+:34]([CH3:43])([CH3:41])[CH:35]5[CH2:40][CH2:39][O:38][CH2:37][CH2:36]5)=[CH:31][CH:32]=4)=[O:25])=[CH:17][C:16]=3[CH:42]=2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 9960124HCID 9960124, compound

Product 1

HCID 21995814HCID 21995814, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(4-butoxyphenyl)-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (300 mg) in DMF (7 ml) was added at room temperature methyl iodide (63 μl), and the mixture was stirred for 18 hours and concentrated under reduced pressure. To the residue was added ethyl acetate, and the resulting crystals were collected by filtration and recrystallized from ethanol to give pale yellow of crystals N-[4-[[7-(4-butoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carbonyl]amino]benzyl]-N,N-dimethyltetrahydro-2H-pyran-4-aminium iodide (Compound 149) (290 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added ethyl acetate
  3. filtrationthe resulting crystals were collected by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-dc7d80518c12452fa5e48a96468bd1f3
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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