Methyl iodide → N-Methyl-N-{3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoyl}-benzenesulfonamide

HRID 1747341Notes

Reaction equation

HRID 1747341 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[N:14]([CH:21]([CH2:35][CH2:36][CH3:37])[CH2:22][C:23]([NH:25][S:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)(=[O:28])=[O:27])=[O:24])[C:13]3=[O:38])=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.IC.[C:41](=O)([O-])[O-].[Cs+].[Cs+].[NH4+].[Cl-]>O.CN(C=O)C>[CH3:41][N:25]([C:23](=[O:24])[CH2:22][CH:21]([N:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:12]([CH2:11][C:9]2[C:10]3[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=3[S:7][CH:8]=2)[C:13]1=[O:38])[CH2:35][CH2:36][CH3:37])[S:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:28])=[O:27]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 25125554N-{3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]hexanoyl}-benzenesulfonamide

Product 1

HCID 59497271N-Methyl-N-{3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoyl}-benzenesulfonamideYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

N-{3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoyl}-benzenesulfonamide (33 mg, 0.061 mmol) and Iodomethane (0.015 mL, 0.24 mmol) are added into DMF (1.0 mL) at room temperature. Then cesium carbonate (80 mg, 0.24 mmol) is added and the mixture is warmed up to 65° C. for 10 min. Then it is cooled down to room temperature for 16 hrs. Saturated NH4Cl solution (3.0 mL) and water (10 mL) are added and the mixture is extracted with EtOAc (3×20 mL). The organic layers are combined, dried (MgSO4) and concentrated to give crude product. Purification by flash column chromatography using EtOAc in hexanes (from 0% to 30%) affords 24 mg (71%) of N-Methyl-N-{3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoyl}-benzenesulfonamide. LCMS (ESMS): m/z 562.19 (M+H+).

Workup

  1. temperatureThen it is cooled down to room temperature for 16 hrs
  2. extractionthe mixture is extracted with EtOAc (3×20 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give crude product
  6. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-3a9757c3a7464de1b5824de89c84f8b4
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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