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

HRID 1815910Notes

Reaction equation

HRID 1815910 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)[N:3]=1.CCN(C(C)C)C(C)C.[NH2:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])=[CH:33][CH:32]=1>>[CH3:20][O:19][C:11]1[CH:10]=[C:9]([NH:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH:30][C:31]3[CH:32]=[CH:33][C:34]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])=[CH:35][CH:36]=3)[N:3]=2)[CH:14]=[C:13]([O:15][CH3:16])[C:12]=1[O:17][CH3:18]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 22028121HCID 22028121, compoundHCID 22496099N-(4-Aminophenyl)prop-2-enamide

Product 1

HCID 10112979N-(4-[4-(3,4,5-trimethoxy-phenylamino)-[1,3,5]triazin-2-ylamino]phenyl}-acrylamide

Conditions

Temperature
100 °C

Procedure

To a slurry of (4-chloro-[1,3,5]triazin-2-yl)-(3,4,5-trimethoxy-phenyl)amine (29.9 mg, 0.101 mmol) in IpOH (2.5 ml) was added DIEA (0.026 mL, 0.151 mmol) and N-(4-aminophenyl)acrylamide (Step 2) (18 mg, 0.111 mmol). The mixture was heated at 100° C. for 18 h. The solution was cooled to RT. The organics were evaporated in vacuo and the residue was purified by column chromatography using 9:1 CH2Cl2/MeOH as the solvent to give N-(4-[4-(3,4,5-trimethoxy-phenylamino)-[1,3,5]triazin-2-ylamino]phenyl}-acrylamide: MS m/z 423[M+H]+. Calc'd for C21H22N6O4: 422.17.

Workup

  1. temperatureThe solution was cooled to RT
  2. customThe organics were evaporated in vacuo
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ad5f3ac3a8cb4fda8db3ecdd27735204
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

Loading…