Ethylamine → HCID 68836204, compound

HRID 2112966Notes

Reaction equation

HRID 2112966 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[C:11]([C:13]3[N:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[N:10]3[N:19]=[C:20]([NH2:22])[N:21]=[C:9]3[CH:8]=2)[CH:2]=1.S([N:33]=[C:34]=[O:35])(C1C=CC(C)=CC=1)(=O)=O.[CH2:36](N)[CH3:37]>CN(C=O)C.C1COCC1>[CH2:36]([NH:33][C:34]([NH:22][C:20]1[N:21]=[C:9]2[CH:8]=[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:12]=[C:11]([C:13]3[N:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[N:10]2[N:19]=1)=[O:35])[CH3:37]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 77703p-Toluenesulfonyl isocyanateHCID 68839691HCID 68839691, compound

Product 1

HCID 68836204HCID 68836204, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A warmed suspension of the product of Step 1 (330 mg, 1.14 mmol) in DMF (10 mL) was treated with TosNCO (0.43 mL, 2.9 mmol). The mixture was stirred at room temperature for 1 h. EtNH2 (14 mL of a 2 M solution in THF) was added all at once and the suspension was heated in the microwave at 100° C. for 12 min. On cooling to 0° C. for 1 h, the precipitated solid 1-ethyl-3-(7-pyridin-3-yl-5-pyrimidin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-urea was collected by filtration, washed with MeOH and dried in vacuo at 80° C. for 2 h. MS m/z 361 (M+H+).

Workup

  1. temperaturewas heated in the microwave at 100° C. for 12 min
  2. temperatureOn cooling to 0° C. for 1 h
  3. filtrationthe precipitated solid 1-ethyl-3-(7-pyridin-3-yl-5-pyrimidin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-urea was collected by filtration
  4. washwashed with MeOH
  5. customdried in vacuo at 80° C. for 2 h

Sources & evidence

ORD record
ord-9004e400c6314ca6897901dc0908ac67
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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