Potassium Carbonate → (E)-N-{5-[2-(1H-Indazol-3-yl)vinyl]-2-(2-morpholinoethoxy)phenyl}methanesulfonamide

HRID 2075437Notes

Reaction equation

HRID 2075437 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[CH:9]=O)(=[O:4])=[O:3].[I-].[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([CH2:33][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:25]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26](/[CH:33]=[CH:9]/[C:8]2[CH:11]=[CH:12][C:13]([O:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:7]=2)=[N:25]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 231178953-Methanesulfonylamino-4-(2-morpholinoethoxy)benzaldehydeHCID 178506551HCID 178506551, compound

Product 1

HCID 11247720(E)-N-{5-[2-(1H-Indazol-3-yl)vinyl]-2-(2-morpholinoethoxy)phenyl}methanesulfonamideYield 14.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-methanesulfonylamino-4-(2-morpholinoethoxy)benzaldehyde obtained in Step 4 (0.27 g, 0.83 mmol) in DMF (5.0 mL) was added with (1H-indazol-3-ylmethyl)triphenylphosphonium iodide obtained in Step 4 of Example 1 (0.40 g, 0.77 mmol) and potassium carbonate (0.23 g, 1.66 mmol), followed by stirring at room temperature for 2 hours, and further stirring at 60° C. for 11 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure, the crude product was purified by silica gel chromatography [amino-modified chemically bound silica gel Chromatorex (registered trademark) NH, Fuji Silysia Chemical Ltd.; ethyl acetate, then methanol/ethyl acetate=1/19], was crystallized from ethyl acetate to obtain Compound 7 (0.05 g, 14%).

Workup

  1. stirringfurther stirring at 60° C. for 11 hours
  2. temperatureAfter cooling to room temperature
  3. customthe solvent was evaporated under reduced pressure
  4. customthe crude product was purified by silica gel chromatography [amino-
  5. customethyl acetate, then methanol/ethyl acetate=1/19], was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-d3ddf71c657142a89f18f46998610c07
Source dataset
uspto-grants-2011_04
Patent number
US07919517B2

Reaction notes

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