Sodium Methoxide → HCID 11360470, compound

HRID 2216253Notes

Reaction equation

HRID 2216253 reaction equation
C[O-].[Na+].[NH2:4][C:5]1[S:9][N:8]=[C:7]([CH3:10])[C:6]=1[Cl:11].C([O:14][C:15](=O)[CH2:16][C:17]1[CH:25]=[CH:24][C:23]2[C:19](=[CH:20][N:21]([CH2:26][CH:27]([CH3:29])[CH3:28])[N:22]=2)[CH:18]=1)C>O1CCCC1>[Cl:11][C:6]1[C:7]([CH3:10])=[N:8][S:9][C:5]=1[NH:4][C:15](=[O:14])[CH2:16][C:17]1[CH:25]=[CH:24][C:23]2[C:19](=[CH:20][N:21]([CH2:26][CH:27]([CH3:28])[CH3:29])[N:22]=2)[CH:18]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 112405714-Chloro-3-methyl-1,2-thiazol-5-amineHCID 21941242HCID 21941242, compound

Product 1

HCID 11360470HCID 11360470, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium methoxide (0.42 g, 0.0078 mol) was added to a solution of 5-amino-4-chloro-3-methylisothiazole (0.46 g, 0.0031 mol) in tetrahydrofuran (THF) (15 ml) and the mixture was stirred at ambient temperature for 15 minutes. A solution of ethyl[2-(2-methylpropyl)indazol-5-yl]acetate (0.80 g, 0.0031 mol) in THF was added dropwise and, once the addition was complete, the mixture was stirred at ambient temperature for 3 hours. The mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution and then the organic extract was dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was triturated with diethyl ether to give N-(4-chloro-3-methylisothiazol-5-yl)-[2-(2-methylpropyl)indazol-5-yl]acetamide (0.78 g) as a pale-brown solid (m.p. 133–135° C.).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 3 hours
  2. customThe mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution
  3. extractionthe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated in vacuo
  7. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-5a69eb4624a34353a03ad6034cd24dbc
Source dataset
uspto-grants-2006_09
Patent number
US07112553B1

Reaction notes

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