Water → HCID 58577252, compound

HRID 1429940Notes

Reaction equation

HRID 1429940 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C: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][CH:15]=3)[CH:10]=[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]=[C:11]3[C:16](=[CH:15][CH:14]=2)[N:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=2)[N:9]=[CH:10]3)[C:18]1=[O:26])[CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 6340IodoethaneHCID 58577650HCID 58577650, compound

Product 1

HCID 58577252HCID 58577252, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-[1-(5-methylpyridin-2-yl)-1H-indazol-5-yl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (70 mg) and iodoethane (35.1 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 (25.0 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-9e39b343b2224d369114d8c925305c61
Source dataset
uspto-grants-2015_01
Patent number
US08940758B2

Reaction notes

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