Methyl iodide → HCID 58148078, compound

HRID 1879946Notes

Reaction equation

HRID 1879946 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[C:17]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH:18]=[C:19]([N:20]3[CH2:24][CH2:23][N:22]([CH3:25])[C:21]3=[O:26])[C:12]2=[N:11][C:10]=1[C:33](=[S:35])[NH2:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:36](N(C(C)C)CC)(C)C.CI>C1COCC1>[CH3:36][S:35][C:33]([C:10]1[N:11]=[C:12]2[C:19]([N:20]3[CH2:24][CH2:23][N:22]([CH3:25])[C:21]3=[O:26])=[CH:18][C:17]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:16][N:13]2[C:14](=[O:15])[C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[NH:34]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 58148053HCID 58148053, compound

Product 1

HCID 58148078HCID 58148078, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the product of example 74 (250 mg, 0.5 mmol) in THF (20 ml) was added diisopropyl ethylamine (65 mg, 0.5 mmol) and methyl iodide (140 mg, 1 mmol), and the mixture was stirred at 60° C. for 1.5 h. The reaction mixture was added ice water, and extracted with ethyl acetate. The organic layer was washed with saturated sodium hydrogen carbonate solution and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give title product (190 mg, 74%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium hydrogen carbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-662eb9d6089f43fe852c2448b78472ff
Source dataset
uspto-grants-2012_11
Patent number
US08318732B2

Reaction notes

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