Thiophene → HCID 14677571, compound

HRID 330546Notes

Reaction equation

HRID 330546 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[N:10]=[C:9]2[NH:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:4][CH:3]=1.S1C=CC=[CH:25]1.[H][H]>CO.[Pt]>[CH3:1][C:2]1[O:6][C:5]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[N:10]=[C:9]2[NH:17][CH:18]2[CH2:23][CH2:22][N:21]([CH3:25])[CH2:20][CH2:19]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8030ThiopheneHCID 60531NoberastineHCID 178418361HCID 178418361, compoundHCID 178486302HCID 178486302, compound

Product 1

HCID 14677571HCID 14677571, compoundYield 14.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 2 parts of poly(oxymethylene), 4.5 parts of 3-[(5-methyl-2-furanyl)methyl]-N-(4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amine, 1 part of a solution of thiophene in methanol 4% and 120 parts of methanol was hydrogenated at normal pressure and at 50° C. with 2 parts of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off over diatomaceous earth 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, (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 0.7 parts (14.3%) of 3-[(5-methyl-2-furanyl)methyl]-N-(1-methyl-4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amine; mp. 131.0° C. (compound 1).

Workup

  1. filtrationthe catalyst was filtered off over diatomaceous earth
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-806268a8e1f5495f9798b26239c313a8
Source dataset
uspto-grants-1990_01
Patent number
US04897401

Reaction notes

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