Ethylamine → HCID 68838124, compound

HRID 2112986Notes

Reaction equation

HRID 2112986 reaction equation
S([N:11]=[C:12]=[O:13])(C1C=CC(C)=CC=1)(=O)=O.[CH3:14][N:15]([CH:32]1[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]1)[C:16]1[N:21]2[N:22]=[C:23]([NH2:25])[N:24]=[C:20]2[CH:19]=[C:18]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH:17]=1.[CH2:39](N)[CH3:40]>CN(C=O)C.C1COCC1>[CH2:39]([NH:11][C:12]([NH:25][C:23]1[N:24]=[C:20]2[CH:19]=[C:18]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH:17]=[C:16]([N:15]([CH3:14])[CH:32]3[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]3)[N:21]2[N:22]=1)=[O:13])[CH3:40]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 77703p-Toluenesulfonyl isocyanateHCID 86618029HCID 86618029, compound

Product 1

HCID 68838124HCID 68838124, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

TosNCO (0.38 g, 1.93 mmol) was added to a solution of the product of Step 1 (0.26 g, 0.77 mmol) in DMF (2.5 mL). After stirring at room temperature for 24 h, ethylamine (3.5 mL of a 2 M solution in THF, 7 mmol) was added to the homogeneous solution, from which a solid precipitated immediately. The mixture was microwaved at 120° C. for 10 min. After cooling to 5° C. for 1 h, a precipitate was collected by filtration, washed with a small volume of MeOH and dried in vacuo at 60° C. to yield 1-ethyl-3-(5-[methyl-(1-methyl-piperidin-4-yl)-amino]-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-urea. MS m/z 409 (M+H+).

Workup

  1. customprecipitated immediately
  2. customThe mixture was microwaved at 120° C. for 10 min
  3. temperatureAfter cooling to 5° C. for 1 h
  4. filtrationa precipitate was collected by filtration
  5. washwashed with a small volume of MeOH
  6. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-7095101e63ab47bf989d936fd442f75d
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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