Sodium Carbonate → HCID 13769657, compound

HRID 979930Notes

Reaction equation

HRID 979930 reaction equation
Br[C:2]1[S:3][C:4]([CH3:7])=[N:5][N:6]=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+]>CN(C)C(=O)C>[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[S:3][C:4]([CH3:7])=[N:5][N:6]=3)[CH2:12][CH2:13]2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 71719042-Bromo-5-methyl-1,3,4-thiadiazoleHCID 12891741N-[1-(2-aminoethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine

Product 1

HCID 13769657HCID 13769657, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2.41 parts of 2-bromo-5-methyl-1,3,4-thiadiazole, 5.5 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-amine, 1.6 parts of sodium carbonate and 45 parts of N,N-dimethylacetamide was stirred and heated overnight at 120° C. The reaction mixture was cooled and poured onto water. 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 saturated with ammonia, (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 2.5 parts (35.8%) of 1-[(4-fluorophenyl)methyl]-N-[1-[2-[(5-methyl-1,3,4-thiadiazol-2-yl)amino]ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 190.6° C. (compound 15).

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionpoured onto water
  3. extractionThe product was extracted with 4-methyl-2-pentanone
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol saturated with ammonia, (96:4 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-7d95f127d6054b658804f24fc64160d6
Source dataset
uspto-grants-1987_01
Patent number
US04634704

Reaction notes

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