1,1'-Carbonyldiimidazole → HCID 178508490, compound

HRID 253954Notes

Reaction equation

HRID 253954 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=2[F:19])=[N:9][NH2:10])=[N:4][CH:5]=[CH:6][N:7]=1.C1N=CN([C:25](N2C=NC=C2)=[O:26])C=1>C1COCC1>[NH2:1][C:2]1[C:3]([C:8]2[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=3[F:19])[C:25]([OH:26])=[N:10][N:9]=2)=[N:4][CH:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178514391HCID 178514391, compound

Product 1

HCID 178508490HCID 178508490, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Amino-N-(2,3-difluorophenyl)-N′-aminopyrazine-2-carboxamidine (500 mg, 1.89 mmol) was dissolved in dry THF (10 mL) and CDI (340 mg, 2.10 mmol) was added at RT. The solution was kept at RT for overnight. After the solvent was removed by evaporation, the residue was added to saturated NaHCO3 solution and filtered. After washing with water, the crude yellow solid product (500 mg, 91%) was obtained after drying under vacuum. LC-MS m/e=290.8 (M+H). Using the same procedure, 5-(3-aminopyrazin-2-yl)-4-(2,3-dichlorophenyl)-4H-1,2,4-triazol-3-ol, 5-(3-aminopyrazin-2-yl)-4-(3-chloro-2-fluorophenyl)-4H-1,2,4-triazol-3-ol, 5-(2-aminopyridin-3-yl)-4-(2,3-difluorophenyl)-4H-1,2,4-triazol-3-ol, 5-(2-aminopyridin-3-yl)-4-(2,3-dichlorophenyl)-4H-1,2,4-triazol-3-ol, and 5-(2-aminopyridin-3-yl)-4-(3-chloro-2-fluorophenyl)-4H-1,2,4-triazol-3-ol can be produced from 3-amino-N-(2,3-dichlorophenyl)-N′-aminopyrazine-2-carboxamidine, 3-amino-N-(3-chloro-2-fluorophenyl)-N′-aminopyrazine-2-carboxamidine, 2-amino-N-(2,3-difluorophenyl)-N′-aminopyridine-3-carboxamidine, 2-amino-N-(2,3-dichlorophenyl)-N′-aminopyridine-3-carboxamidine, and 2-amino-N-(3-chloro-2-fluorophenyl)-N′-aminopyridine-3-carboxamidine, respectively.

Workup

  1. customAfter the solvent was removed by evaporation
  2. additionthe residue was added to saturated NaHCO3 solution
  3. filtrationfiltered
  4. washAfter washing with water

Sources & evidence

ORD record
ord-b86aafe29c0f4ee99bc1919a01aee4ad
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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