2-Chloropyrimidine → 2-Aminobenzimidazole

HRID 1534741Notes

Reaction equation

HRID 1534741 reaction equation
ClC1N=CC=CN=1.NCCN1CCC([NH:17][C:18]2[N:22](CC3C=CC(F)=CC=3)[C:21]3[CH:31]=[CH:32][CH:33]=[CH:34][C:20]=3[N:19]=2)CC1.C(=O)([O-])O.[Na+]>C(O)C>[NH:19]1[C:20]2[CH:34]=[CH:33][CH:32]=[CH:31][C:21]=2[N:22]=[C:18]1[NH2:17]

Participants

5

Reactant 3

HCID 744042-ChloropyrimidineHCID 516892Sodium BicarbonateHCID 12891741N-[1-(2-aminoethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine

Product 1

HCID 136242-Aminobenzimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 34.5 parts of 2-chloropyrimidine, 110 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-amine, 25 parts of sodium hydrogen carbonate and 1200 parts of ethanol was stirred and refluxed overnight. The reaction mixture was cooled and filtered over Hyflo. The filtrate was evaporated. The residue was purified by HPLC over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) saturated with ammonia, as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 82 parts (61%) of 1-[(4-fluorophenyl)methyl]-N-[1-[(2-pyrimidinyl)amino]-ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 168.4° C. (compound 1).

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered over Hyflo
  4. customThe filtrate was evaporated
  5. customThe residue was purified by HPLC over silica gel using
  6. additiona mixture of trichloromethane and methanol (95:5 by volume) saturated with ammonia
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-bf2e824345ce43bc89d7cceb15736759
Source dataset
uspto-grants-1992_02
Patent number
USRE033833

Reaction notes

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