Sodium Hydroxide → N-(3-methylisothiazol-5-yl)-2-[1-(3-methylisoxazol-5-ylmethyl)-1H-indol-3-yl]-2-oxoacetamide

HRID 913185

Reaction equation

HRID 913185 reaction equation
[N:1]1([CH2:10][C:11]2[O:15][N:14]=[C:13]([CH3:16])[CH:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:17](Cl)(=[O:21])[C:18](Cl)=[O:19].[CH3:23][C:24]1[CH:28]=[C:27]([NH2:29])[S:26][N:25]=1.[OH-].[Na+]>C(OCC)C.O1CCCC1.C(N(CC)CC)C>[CH3:23][C:24]1[CH:28]=[C:27]([NH:29][C:17](=[O:21])[C:18]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[N:1]([CH2:10][C:11]3[O:15][N:14]=[C:13]([CH3:16])[CH:12]=3)[CH:2]=2)=[O:19])[S:26][N:25]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 323073-Methylisothiazol-5-amineHCID 65578Oxalyl chlorideHCID 11275877HCID 11275877, compound

Product 1

HCID 10293154N-(3-methylisothiazol-5-yl)-2-[1-(3-methylisoxazol-5-ylmethyl)-1H-indol-3-yl]-2-oxoacetamide

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-(1H-1-indolylmethyl)-3-methylisoxazole (212 mg, 1.0 mmol) in 10 mL diethyl ether was added to oxalyl chloride (254 mg, 2.0 mmol) dropwise at 0° C. The reaction mixture was stirred at 0° C. for 3 hours and then the reaction solvent was evaporated. The residue was dissolved in 5 mL tetrahydrofuran and then the 3-methyl-5-isothiazolamine (114 mg, 1.0 mmol) and triethylamine (1 mL) in 10 mL tetrahydrofuran was added dropwise. The mixture was stirred for 10 hours and then 1 N NaOH (4 mL) was added to the reaction flask dropwise. The mixture was extracted three times with a total of 60 mL of tetrahydrofuran, the organic phase was dried using anhydrous magnesium sulfate and filtered, and the filtrate was concentrated in vacuum. The residue was crystallized from methanol. Yield: 0.27 g, 71%.

Workup

  1. customthe reaction solvent was evaporated
  2. dissolutionThe residue was dissolved in 5 mL tetrahydrofuran
  3. stirringThe mixture was stirred for 10 hours
  4. extractionThe mixture was extracted three times with a total of 60 mL of tetrahydrofuran
  5. customthe organic phase was dried
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuum
  8. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-90f023475c684d8ba878bdf3b848dffe
Source dataset
uspto-grants-2011_09
Patent number
US08026271B2

Linked notes

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