Water → HCID 58577425, compound

HRID 1430071Notes

Reaction equation

HRID 1430071 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-c8c54b9af5384c8f94b45aea55f800b2
Source dataset
uspto-grants-2015_01
Patent number
US08940758B2

Reaction notes

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