Ethanol → HCID 13653876, compound

HRID 280346Notes

Reaction equation

HRID 280346 reaction equation
ClC1C(N)=CC=CN=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]=[C:18]2[NH:26][CH:27]2[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][N:35]=[C:36]=[S:37])[CH2:29][CH2:28]2)=[CH:12][CH:11]=1.[CH2:38]([OH:40])[CH3:39]>>[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]=[C:18]2[NH:26][CH:27]2[CH2:28][CH2:29][N:30]([CH2:33][CH2:34][NH:35][C:36](=[S:37])[O:40][CH2:38][CH3:39])[CH2:31][CH2:32]2)=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 805282-Chloro-3-pyridylamineHCID 128917531-(4-fluorophenylmethyl)-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]1H-benzimidazol-2-amine

Product 1

HCID 13653876HCID 13653876, compound

Procedure

A mixture of 1.3 parts of 2-chloro-3-pyridinamine, 4.1 parts of 1-(4-fluorophenylmethyl)-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]-1H-benzimidazol-2-amine and 80 parts of ethanol was stirred and refluxed overnight. The reaction mixture was evaporated. Water and ammonia were added to the residue and the product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 1.4 parts of ethyl [2-[4-[[1-[(4-fluorophenyl)-methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]carbamothioate; mp. 148.6° C. (compound 35).

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture was evaporated
  3. additionWater and ammonia were added to the residue
  4. extractionthe product was extracted with trichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. customThe residue was crystallized from acetonitrile
  13. filtrationThe product was filtered off
  14. customdried

Sources & evidence

ORD record
ord-1c821b97e1c443248128f1dd4849e78b
Source dataset
uspto-grants-1986_05
Patent number
US04588722

Reaction notes

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