Methyl iodide → HCID 59186228, compound

HRID 336411Notes

Reaction equation

HRID 336411 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:16]3[N:17]=[C:18]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[CH:23][CH:22]=4)[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[OH-].[K+].I[CH3:32]>CS(C)=O>[CH3:32][O:28][CH2:27][C:24]1[CH:23]=[CH:22][C:21]([NH:20][C:18]2[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=[C:11]([C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=4)[N:16]3[N:17]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 59186318HCID 59186318, compound

Product 1

HCID 59186228HCID 59186228, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To the solution of (4-(5-(3-(methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)phenyl)methanol (200 mg, 0.51 mmol) in dimethyl sulfoxide (2 mL) was sequentially added potassium hydroxide (28 mg, 0.51 mmol) and iodomethane. After 3 hr, the reaction mixture was partitioned between water and dichloromethane. The collected organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by preparative thin layer chromatography afforded the desired product (45 mg, 12%). LCMS (ESI) m/z: 409.0.

Workup

  1. customthe reaction mixture was partitioned between water and dichloromethane
  2. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by preparative thin layer chromatography

Sources & evidence

ORD record
ord-803a1cb35a1749e5b8d91dc85d8a683d
Source dataset
uspto-grants-2014_11
Patent number
US08889673B2

Reaction notes

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