Potassium Carbonate → {3-[4-(2-Chloro-benzimidazol-1-yl)-[1,3,5]triazin-2-ylamino]phenyl}acetic acid methyl ester

HRID 983435

Reaction equation

HRID 983435 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]2[N:17]=[C:16](Cl)[N:15]=[CH:14][N:13]=2)[CH:6]=1.[Cl:20][C:21]1[NH:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1.C([O-])([O-])=O.[K+].[K+]>C(C#N)(C)=O>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]2[N:17]=[C:16]([N:22]3[C:23]4[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=4[N:25]=[C:21]3[Cl:20])[N:15]=[CH:14][N:13]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 785722-ChlorobenzimidazoleHCID 23536225[3-(4-Chloro-[1,3,5]triazin-2-ylamino)phenyl]acetic acid methyl ester

Product 1

HCID 23536226{3-[4-(2-Chloro-benzimidazol-1-yl)-[1,3,5]triazin-2-ylamino]phenyl}acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 694302-OxopropiononitrileSolvent

Conditions

Temperature
407.5 °C

Procedure

[3-(4-Chloro-[1,3,5]triazin-2-ylamino)phenyl]acetic acid methyl ester (3.530 g, 12.67 mmol) is combined with 2-chlorobenzimidazole (1.933 g, 12.67 mmol) and K2CO3(2.101 g, 15.20 mmol) in AcCN (50 ml) and heated at 65-750° C. for 2 to 20 hours. The reaction mix is cooled to RT. The inorganic salts are filtered off. The AcCN solution is concentrated down under reduced pressure. The crude is purifired by chromatography with an EtOAc/hexane elution gradient, giving {3-[4-(2-chloro-benzimidazol-1-yl)-[1,3,5]triazin-2-ylamino]phenyl}acetic acid methyl ester.

Workup

  1. additionThe reaction mix
  2. temperatureis cooled to RT
  3. filtrationThe inorganic salts are filtered off
  4. concentrationThe AcCN solution is concentrated down under reduced pressure
  5. washThe crude is purifired by chromatography with an EtOAc/hexane elution gradient

Sources & evidence

ORD record
ord-b70d1f76257a47d8b214e8feebbc294b
Source dataset
uspto-grants-2005_03
Patent number
US06864255B2

Linked notes

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