Ethyl isocyanate → HCID 86618027, compound

HRID 2112975Notes

Reaction equation

HRID 2112975 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[C:4]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:3]=1.[CH2:18]([N:20]=[C:21]=[O:22])[CH3:19]>C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC.C1(C)C=CC=CC=1.C1COCC1>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([NH:11][C:21]([NH:20][CH2:18][CH3:19])=[O:22])[N:10]=[C:6]2[CH:5]=[C:4]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:3]=1

Participants

6

Reactant 2

HCID 8022Ethyl isocyanateHCID 57643138HCID 57643138, compound

Product 1

HCID 86618027HCID 86618027, compound

Reagents, catalysts & solvents 3

HCID 9798523Di-n-butyl diacetoxy tinCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 5-chloro-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine, which may be produced as in Example 1A (210 mg, 0.86 mmol), ethylisocyanate (600 mg, 8.6 mmol), and dibutyltin diacetate (2 drops) in a mixture of toluene and THF (1:1, 10 mL) was heated at 110° C. with stirring in a sealed tube for 5 h. The homogeneous reaction mixture was cooled to RT. The solvent was removed under reduced pressure and the resulting solid was triturated with chloroform (10 mL) and hexanes (250 mL). The solid was filtered, washed with hexanes, and dried to obtain 1-(5-Chloro-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-3-ethyl-urea LCMS (APCI+) 317.

Workup

  1. temperatureThe homogeneous reaction mixture was cooled to RT
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting solid was triturated with chloroform (10 mL) and hexanes (250 mL)
  4. filtrationThe solid was filtered
  5. washwashed with hexanes
  6. customdried

Sources & evidence

ORD record
ord-1514156d016b4fa38c61e4cc8ad86ea7
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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