4-Chlorophenol → 3-(4-(3-(4-chlorophenoxy)propylamino)-1,3,5-triazin-2-ylamino)-N-methylbenzamide

HRID 522888Notes

Reaction equation

HRID 522888 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[N:11]=[CH:10][N:9]=[C:8]([NH:12][C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([NH:18][CH3:19])=[O:17])[N:7]=1.ClC(Cl)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:46][C:47]1[CH:52]=[CH:51][C:50](O)=[CH:49][CH:48]=1.CCOC(/N=N/C(OCC)=O)=O>>[Cl:46][C:47]1[CH:52]=[CH:51][C:50]([O:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]2[N:11]=[CH:10][N:9]=[C:8]([NH:12][C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=3)[C:16]([NH:18][CH3:19])=[O:17])[N:7]=2)=[CH:49][CH:48]=1

Participants

6

Reactant 5

HCID 46844-ChlorophenolHCID 63651,1-DichloroethaneHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 673769083-(4-(3-hydroxypropylamino)-1,3,5-triazin-2-ylamino)-N-methylbenzamide

Product 1

HCID 673758613-(4-(3-(4-chlorophenoxy)propylamino)-1,3,5-triazin-2-ylamino)-N-methylbenzamideYield 20%

Procedure

To a microwave vial charged 3-(4-(3-hydroxypropylamino)-1,3,5-triazin-2-ylamino)-N-methylbenzamide (0.112 g, 0.370 mmol) was added dichloroethane (4 mL), triphenylphosphine (0.146 g, 0.556 mmol), p-chlorophenol (0.095 g, 0.741 mmol)) and DEAD (0.129 g, 0.741 mmol) respectively. The reaction mixture was irradiated in the microwave at 130° C. for 30 min. The reaction mixture was concentrated under reduced pressure and purified with flash chromatography using CH2Cl2:MeOH:NH4OH (90:10:1) in CH2Cl2 to afford 3-(4-(3-(4-chlorophenoxy)propylamino)-1,3,5-triazin-2-ylamino)-N-methylbenzamide (30 mg, 20%) as a white solid.

Workup

  1. customThe reaction mixture was irradiated in the microwave at 130° C. for 30 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified with flash chromatography

Sources & evidence

ORD record
ord-220327a6df5e480996b600b4868e1798
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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