Ethylamine → HCID 68836197, compound

HRID 2112974Notes

Reaction equation

HRID 2112974 reaction equation
[CH:1]1([NH:7][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:34]=[C:35]=[O:36])(C1C=CC(C)=CC=1)(=O)=O.[CH2:37](N)[CH3:38]>CN(C=O)C.C1COCC1>[CH:1]1([NH:7][C:8]2[N:13]3[N:14]=[C:15]([NH:17][C:35]([NH:34][CH2:37][CH3:38])=[O:36])[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 86235182HCID 86235182, compound

Product 1

HCID 68836197HCID 68836197, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product of Step 1 (256 mg, 0.83 mmol) was taken up in DMF (2 mL) and cooled on an ice/water bath. TosNCO (0.18 g, 0.91 mmol) was added all at once. The solution was allowed to stir at room temperature for 1.5 h. Ethylamine (3 mL of a 2 M solution in THF) was added and the resulting solution was microwaved at 120° C. for 10 min. The solution was cooled in the refrigerator overnight and the resulting precipitate was collected by filtration yielding 1-(5-cyclohexylamino-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-3-ethyl-urea. MS m/z 380 (M+H+).

Workup

  1. temperaturecooled on an ice/water bath
  2. customthe resulting solution was microwaved at 120° C. for 10 min
  3. temperatureThe solution was cooled in the refrigerator overnight
  4. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-267e9a3c0c6248f28bcd16050580992a
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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