Sodium Iodide → HCID 68999231, compound

HRID 1821438Notes

Reaction equation

HRID 1821438 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([O:40][CH3:41])=[C:8]([NH:31][C:32]([C:34]2[S:35][CH:36]=[CH:37][C:38]=2[CH3:39])=[O:33])[C:9](/[CH:12]=[CH:13]/[C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16](C(C3SC=CC=3C)=O)[N:15]=2)=[CH:10][CH:11]=1.[CH2:42]([NH:44][CH2:45][CH2:46][OH:47])[CH3:43].[I-].[Na+].[OH-].[Na+]>CN(C)C(=O)C.O>[CH2:42]([N:44]([CH2:45][CH2:46][OH:47])[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([O:40][CH3:41])=[C:8]([NH:31][C:32]([C:34]2[S:35][CH:36]=[CH:37][C:38]=2[CH3:39])=[O:33])[C:9](/[CH:12]=[CH:13]/[C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][N:15]=2)=[CH:10][CH:11]=1)[CH3:43]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 80722-(Ethylamino)ethanolHCID 14798Sodium HydroxideHCID 68999513HCID 68999513, compound

Product 1

HCID 68999231HCID 68999231, compoundYield 34.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of (E)-N-(3-(3-chloropropoxy)-2-methoxy-6-{2-[1-(3-methylthiophene-2-carbonyl)-1H-indazol-3-yl]vinyl}phenyl)-3-methylthiophene-2-carboxamide (0.30 g, 0.49 mmol) obtained in Step 4 in N,N-dimethylacetamide (6.0 mL) was added with 2-(ethylamino)ethanol (0.97 mL, 9.9 mmol) and sodium iodide (0.11 g, 0.74 mmol), followed by stirring at 90° C. for 3.0 hours. After cooling the reaction mixture to room temperature, aqueous sodium hydroxide solution (2.0 mol/L, 3.0 mL) was added and the mixture was stirred for 1.0 hour. The mixture was added with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography [amino-silica gel chromatorex (trade mark) NH, manufactured by Fuji Silysia; hexane/ethyl acetate=60/40 to ethyl acetate] and crystallized from hexane/ethyl acetate (1/1) to obtain Compound 339 (91 mg, 34%).

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. stirringthe mixture was stirred for 1.0 hour
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography [amino-silica gel chromatorex (trade mark) NH, manufactured by Fuji Silysia; hexane/ethyl acetate=60/40 to ethyl acetate]
  6. customcrystallized from hexane/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-f941246f11fa41b3a0304a3edfe6ffed
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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