Sulfur → HCID 178467910, compound

HRID 1708928Notes

Reaction equation

HRID 1708928 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][N:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[N:29]([CH2:30][CH2:31][O:32][CH2:33][CH3:34])[C:24]3=[N:25][CH:26]=[CH:27][CH:28]=[C:23]3[N:22]=2)[CH2:16][CH2:15]1)=S.[S]>[Hg]=O.O1CCCC1>[CH2:33]([O:32][CH2:31][CH2:30][N:29]1[C:24]2=[N:25][CH:26]=[CH:27][CH:28]=[C:23]2[N:22]=[C:21]1[CH2:20][N:17]1[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][NH:11][C:9]2[NH:1][C:2]3[CH:7]=[CH:6][N:5]=[CH:4][C:3]=3[N:8]=2)[CH2:15][CH2:16]1)[CH3:34]

Participants

5

Reactant 2

HCID 5362487SulfurHCID 19911578N-(4-amino-3-pyridinyl)-N'-[2-[4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl)-1-piperazinyl]ethyl]thiourea

Product 1

HCID 178467910HCID 178467910, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 16.9 parts of N-(4-amino-3-pyridinyl)-N'-[2-[4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl)-1-piperazinyl]ethyl]thiourea, 11.4 parts of mercury(II)oxide, 0.1 parts of sulfur and 135 parts of tetrahydrofuran was stirred for 3 hours at reflux temperature. The reaction mixture was filtered while hot over diatomaceous earth and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol, saturated with ammonia, (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was stirred in 2,2'-oxybispropane. The product was filtered off and dried, yielding 4.73 parts (30.0%) of N-[2-[4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperazinyl]ethyl]-1H-imidazo[4,5-c]pyridin-2-amine; mp. 124.5° C. (compound 123).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe reaction mixture was filtered while hot over diatomaceous earth
  3. customthe filtrate was evaporated
  4. customThe residue was purified by column chromatography over silica gel using
  5. additiona mixture of dichloromethane and methanol
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. stirringThe residue was stirred in 2,2'-oxybispropane
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-8ec942aae0c4409cb31d8d5a1a175b26
Source dataset
uspto-grants-1990_08
Patent number
US04946843

Reaction notes

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