Methyl iodide → HCID 86621150, compound

HRID 450108Notes

Reaction equation

HRID 450108 reaction equation
[CH3:1][I:2].[O:3]=[C:4]([C:20]1[N:28]2[C:23]([CH:24]=[CH:25][CH:26]=[CH:27]2)=[CH:22][C:21]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][S:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)=[O:6]>C1COCC1>[I-:2].[CH3:1][S+:17]1[CH2:16][CH2:15][N:14]([C:11]2[CH:12]=[CH:13][C:8]([NH:7][C:5](=[O:6])[C:4](=[O:3])[C:20]3[N:28]4[C:23]([CH:24]=[CH:25][CH:26]=[CH:27]4)=[CH:22][C:21]=3[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[CH:9][CH:10]=2)[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 67106698HCID 67106698, compound

Product 1

HCID 86621150HCID 86621150, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl iodide (1.6 g, 11.26 mmol) was added to a solution of 2-oxo-2-(2-phenyl-indolizin-3-yl)-N-(4-thiomorpholin-4-yl-phenyl)-acetamide (1 g, 2.2 mmol) in anhydrous THF (25 ml) and then heated to reflux for 8 hr. The reaction mixture was cooled and the resultant precipitate was filtered and washed with cold THF. The solid was dried at 40° C. yielding 1-methyl-4-{4-[2-oxo-2-(2-phenyl-indolizin-3-yl)-acetylamino]-phenyl}-thiomorpholin-1-ium iodide (600 mg, 58%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 8 hr
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe resultant precipitate was filtered
  5. washwashed with cold THF
  6. customThe solid was dried at 40° C.

Sources & evidence

ORD record
ord-4394273699694072bd07b2fd373d1393
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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