Methanol → HCID 131716773, compound

HRID 1886423Notes

Reaction equation

HRID 1886423 reaction equation
Cl.[CH3:2][C:3]1[O:7][C:6]([CH2:8][N:9]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:23][CH2:22][NH:21][CH2:20]2)=[CH:5][CH:4]=1.S1C=CC=[CH:25]1.[C:29]([O-:32])(=[O:31])[CH3:30].[K+].[H][H].C[OH:37]>[Pd]>[C:6]([OH:37])(=[O:7])/[CH:8]=[CH:30]/[C:29]([OH:32])=[O:31].[CH3:2][C:3]1[O:7][C:6]([CH2:8][N:9]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:23][CH2:22][N:21]([CH3:25])[CH2:20]2)=[CH:5][CH:4]=1

Participants

8

Reactant 6

HCID 887Methanol2×HCID 8030ThiopheneHCID 517044Potassium AcetateHCID 19875936HCID 19875936, compoundHCID 178418361HCID 178418361, compoundHCID 178486302HCID 178486302, compound

Product 1

HCID 131716773HCID 131716773, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 6 parts of 3-[(5-methyl-2-furanyl)methyl]-N-(3-pyrrolidinyl)-3H-imidazo[4,5-b]pyridin-2-amine monohydrochloride, 2 parts of poly(oxymethylene), 1 part of a solution of thiophene in methanol 4%, 160 parts of methanol and 6 parts of potassium acetate was hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was taken up in water and a small amount of concentrated ammonium hydroxide was added. The product was extracted twice with trichloromethane. The combined extracts were washed with water, dried, filtered and evaporated. The oily residue was converted into the (E)-2-butenedioate salt in 320 parts of 2-propanone. The salt was filtered off, washed with 2-propanone and crystallized from 2-propanol. The product was filtered off and dried in vacuo at 60° C., yielding 1.5 parts (15.3%) of 3 -[(5-methyl-2-furanyl)methyl]-N-(1-methyl-3-pyrrolidinyl)-3H-imidazo[4,5-b]-pyridin-2-amine (E)-2-butenedioate(1:2); mp. 168.6° C. (compound 193).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. additiona small amount of concentrated ammonium hydroxide was added
  4. extractionThe product was extracted twice with trichloromethane
  5. washThe combined extracts were washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. filtrationThe salt was filtered off
  10. washwashed with 2-propanone
  11. customcrystallized from 2-propanol
  12. filtrationThe product was filtered off
  13. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-6beda6870abb4f9488c36d7f1c88fea6
Source dataset
uspto-grants-1992_09
Patent number
US05151424

Reaction notes

Loading…