Potassium Iodide → HCID 13588090, compound

HRID 845788Notes

Reaction equation

HRID 845788 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]2[N:22]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[C:21]3[CH:31]=[CH:32][CH:33]=[CH:34][C:20]=3[N:19]=2)[CH2:13][CH2:12]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O>[F:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][N:22]2[C:21]3[CH:31]=[CH:32][CH:33]=[CH:34][C:20]=3[N:19]=[C:18]2[NH:17][CH:14]2[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][NH:8][C:2]3[N:7]=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:12][CH2:13]2)=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 744042-ChloropyrimidineHCID 12891741N-[1-(2-aminoethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine

Product 1

HCID 13588090HCID 13588090, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.14 parts of 2-chloropyrimidine, 3.7 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine, 1.06 parts of sodium carbonate, 0.1 parts of potassium iodide and 135 parts of N,N-dimethylformamide was stirred and heated overnight at 70° C. The reaction mixture was poured onto water and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (96:4 by volume), saturated with ammonia, as eluent. The pure fractions were collected and tbe eluent was evaporated. The residue was crystallized from acetonitrile, yielding 1.5 parts (34%) of 1-[(4-fluorophenyl)methyl]-N-[1-[2-[(2-pyrimidinyl)amino]ethyl]-4piperidinyl]-1H-benzimidazol -2-amine; mp. 168.4° C. (compound 1).

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionthe product was extracted with 4-methyl-2-pentanone
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column-chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (96:4 by volume)
  8. customThe pure fractions were collected
  9. customtbe eluent was evaporated
  10. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-68781d7b3f7e4e5fbf9120e0dd08179f
Source dataset
uspto-grants-1988_07
Patent number
US04760074

Reaction notes

Loading…