Sulfur → HCID 178505782, compound

HRID 1493936Notes

Reaction equation

HRID 1493936 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([NH:22][C:23]2[N:27]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[C:26]3[CH:36]=[CH:37][CH:38]=[CH:39][C:25]=3[N:24]=2)[CH2:18][CH2:17]1)=S.[S]>[Hg]=O.O1CCCC1>[F:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][N:27]2[C:26]3[CH:36]=[CH:37][CH:38]=[CH:39][C:25]=3[N:24]=[C:23]2[NH:22][CH:19]2[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:9]3[NH:1][C:2]4[CH:7]=[CH:6][N:5]=[CH:4][C:3]=4[N:8]=3)[CH2:17][CH2:18]2)=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 5362487SulfurHCID 14989888HCID 14989888, compound

Product 1

HCID 178505782HCID 178505782, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 18 parts of N-(4-amino-3-pyridinyl)-N'-[4-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]-butyl]thiourea, 7 parts of mercury(II)oxide, 1 part of sulfur and 180 parts of tetrahydrofuran was stirred and refluxed for 5 hours. The reaction mixture was filtered hot 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, (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of tetrahydrofuran and trichloromethane, yielding 5 parts (29%) of N-[4-[4-[[1-[(4-fluorophenyl)-methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]butyl]-1H-imidazo-[4,5-c]pyridin-2-amine; mp. 228.2° C. (compound 121).

Workup

  1. temperaturerefluxed for 5 hours
  2. filtrationThe reaction mixture was filtered hot over Hyflo
  3. customthe filtrate was evaporated
  4. customThe residue was purified by column chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol saturated with ammonia, (90:10 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. customThe residue was crystallized from a mixture of tetrahydrofuran and trichloromethane

Sources & evidence

ORD record
ord-ec8b6f104a084f90add4d8a3bed24dbc
Source dataset
uspto-grants-1991_06
Patent number
US05025014

Reaction notes

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