Water → HCID 58577425, compound

HRID 1044322Notes

Reaction equation

HRID 1044322 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:16]=[C:15]3[C:10]([CH:11]=[CH:12][C:13]([N:17]4[C:21]5=[N:22][CH:23]=[CH:24][CH:25]=[C:20]5[NH:19][C:18]4=[O:26])=[CH:14]3)=[N:9]2)=[N:6][CH:7]=1.I[CH2:28][CH3:29].O>CN(C=O)C>[CH2:28]([N:19]1[C:20]2[C:21](=[N:22][CH:23]=[CH:24][CH:25]=2)[N:17]([C:13]2[CH:12]=[CH:11][C:10]3[C:15](=[CH:16][N:8]([C:5]4[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=4)[N:9]=3)[CH:14]=2)[C:18]1=[O:26])[CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 6340IodoethaneHCID 58577288HCID 58577288, compound

Product 1

HCID 58577425HCID 58577425, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-[2-(5-methylpyridin-2-yl)-2H-indazol-5-yl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (31 mg) and iodoethane (15.5 mg) in DMF (2 mL) was stirred at 50° C. for 3 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel eluting with AcOEt/Hexane. The product was crystallized from AcOEt/Hexane to give the title compound as white crystals (5.4 mg).

Workup

  1. extractionextracted with AcOEt
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with AcOEt/Hexane
  5. customThe product was crystallized from AcOEt/Hexane

Sources & evidence

ORD record
ord-acd9f0768c284b07ba17d66bd89543f9
Source dataset
uspto-grants-2013_10
Patent number
US08563575B2

Reaction notes

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