Ethyl isocyanate → HCID 68835955, compound

HRID 2112969Notes

Reaction equation

HRID 2112969 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:7]2[N:12]3[N:13]=[C:14]([NH2:16])[N:15]=[C:11]3[CH:10]=[C:9]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:8]=2)=[CH:5][N:6]=1.[CH2:23]([N:25]=[C:26]=[O:27])[CH3:24]>C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC.C1(C)C=CC=CC=1>[CH2:23]([NH:25][C:26]([NH:16][C:14]1[N:15]=[C:11]2[CH:10]=[C:9]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:8]=[C:7]([C:4]3[S:3][C:2]([CH3:1])=[N:6][CH:5]=3)[N:12]2[N:13]=1)=[O:27])[CH3:24]

Participants

5

Reactant 2

HCID 8022Ethyl isocyanateHCID 68835562HCID 68835562, compound

Product 1

HCID 68835955HCID 68835955, compound

Reagents, catalysts & solvents 2

HCID 9798523Di-n-butyl diacetoxy tinCatalystHCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

A suspension of the product of Step 1 (160 mg, 0.52 mmol), ethylisocyanate (205 μL, 2.6 mmol), and dibutyltin diacetate (5 drops) in dry toluene (6 mL) was heated at 125° C. in a microwave reactor for 1 h. After being cooled at room temperature the precipitated solid was filtered and washed with chloroform. The crude product was purified by flash chromatography (gradient 0-2% methanol/chloroform) to give 1-ethyl-3-[5-(2-methyl-thiazol-5-yl)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-urea as a solid. MS m/z 380 (M+H+).

Workup

  1. temperatureAfter being cooled at room temperature the precipitated solid
  2. filtrationwas filtered
  3. washwashed with chloroform
  4. customThe crude product was purified by flash chromatography (gradient 0-2% methanol/chloroform)

Sources & evidence

ORD record
ord-7f370f825fe44681b848c16f128365bc
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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