Potassium Carbonate → HCID 22560089, compound

HRID 983436Notes

Reaction equation

HRID 983436 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]3[CH:20]=[CH:19][N:18]=[N:17]3)[CH:10]=2)[N:3]=1.[Cl:21][C:22]1[NH:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1.C([O-])([O-])=O.[K+].[K+]>C(C#N)(C)=O.CO.C(Cl)Cl>[Cl:21][C:22]1[N:26]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]4[CH:20]=[CH:19][N:18]=[N:17]4)[CH:10]=3)[N:3]=2)[C:25]2[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=2[N:23]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 785722-ChlorobenzimidazoleHCID 22560109HCID 22560109, compound

Product 1

HCID 22560089HCID 22560089, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 694302-OxopropiononitrileSolvent

Conditions

Temperature
70 °C

Procedure

(4-Chloro-[1,3,5]triazin-2-yl)-(3-[1,2,3]triazol-1-ylmethyl-phenyl)-amine (552.7 mg, 1.921 mmol) is combined with 2-chlorobenzimidazole (381 mg, 2.497 mmol) and K2CO3 (372 mg, 2.689 mmol) in AcCN (10 ml) and heated at 65-75° C. for 2 to 20 h. The reaction mix is cooled to RT and diluted with MeOH and CH2Cl2. The inorganic salts are filtered off and the organic solution is concentrated under reduced pressure. The crude is treated with AcCN (5-8 ml), forming a precipitate. The precipitate is filtered and dried, giving [4-(2-chloro-benzoimidazol-1-yl)-[1,3,5]triazin-2-yl]-(3-[1,2,3]triazol-1-ylmethyl-phenyl)-amine.

Workup

  1. additionThe reaction mix
  2. temperatureis cooled to RT
  3. filtrationThe inorganic salts are filtered off
  4. concentrationthe organic solution is concentrated under reduced pressure
  5. additionThe crude is treated with AcCN (5-8 ml)
  6. customforming a precipitate
  7. filtrationThe precipitate is filtered
  8. customdried

Sources & evidence

ORD record
ord-f7bbe33f66d24b6d9b8d31400f5dfe08
Source dataset
uspto-grants-2005_03
Patent number
US06864255B2

Reaction notes

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