Ethylamine → HCID 68835013, compound

HRID 2112972Notes

Reaction equation

HRID 2112972 reaction equation
[CH:1]1([N:7]([CH3:24])[C:8]2[N:13]3[N:14]=[C:15]([NH2:17])[N:16]=[C:12]3[CH:11]=[C:10]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S([N:35]=[C:36]=[O:37])(C1C=CC(C)=CC=1)(=O)=O.[CH2:38](N)[CH3:39]>CN(C=O)C.C1COCC1>[CH:1]1([N:7]([CH3:24])[C:8]2[N:13]3[N:14]=[C:15]([NH:17][C:36]([NH:35][CH2:38][CH3:39])=[O:37])[N:16]=[C:12]3[CH:11]=[C:10]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 6341EthylamineHCID 77703p-Toluenesulfonyl isocyanateHCID 86618026HCID 86618026, compound

Product 1

HCID 68835013HCID 68835013, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product of Step 1 (290 mg, 0.90 mmol) was taken up in DMF (1 mL). TosNCO (0.44 g, 2.3 mmol) was added all at once. The solution became warm and was allowed to cool to room temperature over 1 h. Ethylamine (6 mL of a 2 M solution in THF) was added and the resulting mixture was microwaved at 100° C. for 10 min then at 120° C. for 30 min. The resulting solid was collected by filtration and triturated with CH2Cl2/MeOH to afford 1-[5-(cyclohexyl-methyl-amino)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-3-ethyl-urea. MS m/z 394 (M+H+).

Workup

  1. temperatureThe solution became warm
  2. customthe resulting mixture was microwaved at 100° C. for 10 min
  3. filtrationThe resulting solid was collected by filtration
  4. customtriturated with CH2Cl2/MeOH

Sources & evidence

ORD record
ord-d3210ede484542a6bece7eb00185a7e0
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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