Methyl iodide → HCID 69275118, compound

HRID 2219217Notes

Reaction equation

HRID 2219217 reaction equation
[C:1]([O-])([O-])=O.[K+].[K+].[C:7]([O:11][C:12](=[O:46])[N:13]([CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:14][CH2:15][NH:16][S:17]([C:20]1[C:21]2[CH:22]=[CH:23][N:24]=[CH:25][C:26]=2[CH:27]=[CH:28][CH:29]=1)(=[O:19])=[O:18])([CH3:10])([CH3:9])[CH3:8].CI>CN(C=O)C.CCOC(C)=O>[C:7]([O:11][C:12](=[O:46])[N:13]([CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[CH2:14][CH2:15][N:16]([S:17]([C:20]1[C:21]2[CH:22]=[CH:23][N:24]=[CH:25][C:26]=2[CH:27]=[CH:28][CH:29]=1)(=[O:19])=[O:18])[CH3:1])([CH3:10])([CH3:8])[CH3:9]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 69275014HCID 69275014, compound

Product 1

HCID 69275118HCID 69275118, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Powdered K2CO3 (50.4 mg, 0.365 mmol) is added to a stirred solution of [2-(2-benzyl-phenoxy)-ethyl]-[2-(isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester (82.0 mg, 0.146 mmol) and CH3I (18.2 μL, 0.292 mmol) in anhydrous DMF (1 mL) at ambient temperature under nitrogen. The resultant solution is stirred for 2 hours. The mixture is diluted with EtOAc (10 mL), washed with water (5 mL×3), dried over MgSO4, filtered and concentrated. The crude product is chromatographed on silica (gradient 0-5% CH3OH in CH2Cl2) to give 65 mg (0.11 mmol, 77% yield) of the title compound as a gum. ESIMS: m/z 576 (M+H)+.

Workup

  1. washwashed with water (5 mL×3)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is chromatographed on silica (gradient 0-5% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-6e49b5dadf0c43569c4831292cbdf80f
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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