Diisopropylethylamine → N-{3-[4-(3-chlorophenylamino)-[1,3,5]triazin-2-ylamino]-phenyl}-acrylamide

HRID 1815921Notes

Reaction equation

HRID 1815921 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13](Cl)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.[NH2:25][C:26]1[CH:27]=[C:28]([NH:32][C:33](=[O:36])[CH:34]=[CH2:35])[CH:29]=[CH:30][CH:31]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:10]=[CH:11][N:12]=[C:13]([NH:25][C:26]3[CH:27]=[C:28]([NH:32][C:33](=[O:36])[CH:34]=[CH2:35])[CH:29]=[CH:30][CH:31]=3)[N:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 22028113(3-Chlorophenyl)-(4-chloro-[1,3,5]triazin-2-yl)amineHCID 22033841N-(3-aminophenyl)acrylamide

Product 1

HCID 10270290N-{3-[4-(3-chlorophenylamino)-[1,3,5]triazin-2-ylamino]-phenyl}-acrylamide

Conditions

Temperature
100 °C

Procedure

To a slurry of (3-chlorophenyl)-(4-chloro-[1,3,5]triazin-2-yl)amine (Step 1) (80.0 mg, 0.332 mmol) in IpOH (2.5 ml) was added DIEA (0.087 mL, 0.50 mmol) and N-(3-aminophenyl)acrylamide (59.2 mg, 0.365 mmol). The mix was heated at 100° C. for 18 h. The solution was then cooled to RT. A precipitate fell out of solution, was filtered off and dried under reduced pressure to give N-{3-[4-(3-chlorophenylamino)-[1,3,5]triazin-2-ylamino]-phenyl}-acrylamide: MS m/z=367[M+H]. Calc'd for C18H15ClN6O: 366.10.

Workup

  1. temperatureThe solution was then cooled to RT
  2. filtrationwas filtered off
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-1ce7e165dd454f4d83267f7455413ad3
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

Loading…