Ethanol → HCID 19890733, compound

HRID 893691Notes

Reaction equation

HRID 893691 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][NH:27][C:28]([NH:30][C:31]3[CH:32]=[N:33][CH:34]=[CH:35][C:36]=3[NH:37][CH3:38])=S)[CH2:21][CH2:20]2)=[CH:4][CH:3]=1.[S].C([OH:42])C>[Hg]=O>[OH2:42].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][NH:27][C:28]3[N:37]([CH3:38])[C:36]4[CH:35]=[CH:34][N:33]=[CH:32][C:31]=4[N:30]=3)[CH2:21][CH2:20]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 5362487SulfurHCID 14989883HCID 14989883, compound

Product 1

HCID 19890733HCID 19890733, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 30856Mercuric oxideCatalyst2×

Procedure

A mixture of 8 parts of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-N'-[4-(methylamino)-3-pyridinyl]thiourea, 15 parts of mercury(II)oxide, 0.1 parts of sulfur and 120 parts of ethanol was stirred and refluxed for 3 hours. After the addition of another 15 parts of mercury(II)oxide, stirring at reflux was continued for 2 hours. The reaction mixture was filtered over Hyflo and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol saturated with ammonia (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile. The produce was filtered off and dried, yielding 4.4 parts (59%) of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-1-methyl-1H-imidazo[4,5-c]pyridin-2-amine monohydrate; mp. 144.6° C. (compound 108).

Workup

  1. temperaturerefluxed for 3 hours
  2. stirringstirring
  3. temperatureat reflux
  4. filtrationThe reaction mixture was filtered over Hyflo
  5. customthe filtrate was evaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol saturated with ammonia (95:5 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from acetonitrile
  11. filtrationThe produce was filtered off
  12. customdried

Sources & evidence

ORD record
ord-68b1ad2b7e7c4367b07e6c05b61ebff8
Source dataset
uspto-grants-1992_06
Patent number
US05126339

Reaction notes

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