Potassium Carbonate → HCID 22496137, compound

HRID 1815897Notes

Reaction equation

HRID 1815897 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[C:11]([CH2:15][C:16]([NH2:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[N:3]=1.[Cl:19][C:20]1[NH:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=1.C(=O)([O-])[O-].[K+].[K+]>C(C#N)(C)=O>[Cl:19][C:20]1[N:24]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]3[CH:10]=[C:11]([CH2:15][C:16]([NH2:18])=[O:17])[CH:12]=[CH:13][CH:14]=3)[N:3]=2)[C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[N:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 785722-ChlorobenzimidazoleHCID 22496152HCID 22496152, compound

Product 1

HCID 22496137HCID 22496137, compound

Reagents, catalysts & solvents 1

HCID 694302-OxopropiononitrileSolvent

Conditions

Temperature
70 °C

Procedure

2-[3-(4-Chloro-[1,3,5]triazin-2-ylamino)-phenyl]-acetamide (136.5 mg, 0.5177 mmol) is combined with 2-chlorobenzimidazole (86.9 mg, 0.5177 mmol) and potassium carbonate (93 mg, 0.673 mmol) in AcCN (5 ml) and heated at 65-75° C. for 2 to 20 hours. The reaction mix is cooled to RT and the inorganic salts were filtered off. The AcCN solution is concentrated down under reduced pressure. The crude is purified on a silica gel column with an EtOAc/hexane to MeOH/CH2Cl2 elution gradient, giving 2-{3-[4-(2-chloro-benzoimidazol-1-yl)-[1,3,5]triazin-2-ylamino]-phenyl}acetamide.

Workup

  1. additionThe reaction mix
  2. temperatureis cooled to RT
  3. filtrationthe inorganic salts were filtered off
  4. concentrationThe AcCN solution is concentrated down under reduced pressure
  5. customThe crude is purified on a silica gel column with an EtOAc/hexane to MeOH/CH2Cl2 elution gradient

Sources & evidence

ORD record
ord-29e9532215f5405aa197aa2946fa79cd
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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