Benzaldehyde → HCID 67213120, compound

HRID 2223827Notes

Reaction equation

HRID 2223827 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH3:11])[CH3:10])[N:5]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.CN(C)C=O.[F:24][C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH2:27].Cl.O1CCOCC1.C(O)C(N)(CO)CO.C(=O)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>CN1CCCC1=O.C(Cl)(Cl)Cl>[F:24][C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH:27][C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH3:11])[CH3:10])[N:5]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1

Participants

9

Reactant 6

HCID 240BenzaldehydeHCID 6503Tris(hydroxymethyl)aminomethaneHCID 516892Sodium BicarbonateHCID 7907666-chloro-4-N-phenyl-2-N-propan-2-yl-1,3,5-triazine-2,4-diamineHCID 204431481,4-Dioxane hydrochlorideHCID 23033167HCID 23033167, compound

Product 1

HCID 67213120HCID 67213120, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

A 14 mg portion of 6-chloro-N-isopropyl-N′-phenyl-1,3,5-triazine-2,4-diamine was dissolved in 800 μl of N-methyl-2-pyrrolidone, and 200 μl of 0.5 mM 2-fluoroaniline N,N-dimethylformamide solution and 50 μl of 4 M hydrochloric acid/dioxane were added thereto and stirred at 80° C. for 7 hours. After cooling down the reaction solution to 60° C., 50 mg (4.27 mmol/g) of PS-trisamine and 50 mg (1.53 mmol/g) of PS-benzaldehyde both manufactured by Algonote were added to the reaction solution and further stirred at 60° C. for 16 hours. The reaction solution was cooled down to room temperature and then mixed with saturated sodium bicarbonate aqueous solution and chloroform and stirred. After filtration of the solution, the organic layer was dried using anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure to obtain 13 mg of N-(2-fluorophenyl)-N′-isopropyl-N″-phenyl-1,3,5-triazine-2,4,6-triamine as a brown resinous substance.

Workup

  1. temperatureAfter cooling down the reaction solution to 60° C.
  2. additionwere added to the reaction solution
  3. stirringfurther stirred at 60° C. for 16 hours
  4. temperatureThe reaction solution was cooled down to room temperature
  5. stirringstirred
  6. filtrationAfter filtration of the solution
  7. customthe organic layer was dried
  8. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-adfed781310f452c884a0e15a1bcb7d7
Source dataset
uspto-grants-2008_05
Patent number
US07375222B2

Reaction notes

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