Acetic Acid → 3-(2-furanylmethyl)-3H-imidazo[4,5-b]pyridin-2-amine

HRID 704714Notes

Reaction equation

HRID 704714 reaction equation
N#N.O1C=CC=C1C[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[C:10]=1[NH2:16].N=COC[NH:21][C:22](=O)OC.[C:26]([OH:29])(=O)[CH3:27].[CH3:30][C:31]1C=CC=C[CH:32]=1>>[O:29]1[CH:32]=[CH:31][CH:30]=[C:26]1[CH2:27][N:15]1[C:11]2=[N:12][CH:13]=[CH:14][CH:9]=[C:10]2[N:16]=[C:22]1[NH2:21]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 15037334Methyl (iminomethoxymethyl)-carbamateHCID 86744557N2 (2-furanylmethyl)-2,3-pyridinediamine

Product 1

HCID 156239903-(2-furanylmethyl)-3H-imidazo[4,5-b]pyridin-2-amineYield 51%

Procedure

A mixture of 47.5 parts of N2 -(2-furanylmethyl)-2,3-pyridinediamine, 36.5 parts of methyl (iminomethoxymethyl)carbamate, 34.5 parts of acetic acid and 450 parts of methylbenzene was stirred and heated for 16 hours at 65°~68° C. The reaction mixture was evaporated. 140 Parts of potassium hydroxide, 50 parts of water and 400 parts of 2-propanol were added to the residue and stirring was continued for 16 hours at reflux. The reaction mixture was concentrated to 1/4 of its volume. 500 Parts of water were added and 2-propanol was distilled off azeotropically. After stirring for 1 hour at room temperature, the product was filtered off, washed successively twice with 20 parts of water and three times with 12 parts of 2-propanone and crystallized from 1,2-dichloroethane. The product was filtered off and dried in vacuo at 50° C., yielding 27.3 parts (51.0%) of 3-(2-furanylmethyl)-3H-imidazo[4,5 -b]pyridin-2-amine; mp. 193.3° C. (interm. 32).

Workup

  1. temperatureheated for 16 hours at 65°~68° C
  2. customThe reaction mixture was evaporated
  3. addition140 Parts of potassium hydroxide, 50 parts of water and 400 parts of 2-propanol were added to the residue
  4. stirringstirring
  5. temperatureat reflux
  6. concentrationThe reaction mixture was concentrated to 1/4 of its volume
  7. addition500 Parts of water were added
  8. distillation2-propanol was distilled off azeotropically
  9. stirringAfter stirring for 1 hour at room temperature
  10. filtrationthe product was filtered off
  11. washwashed successively twice with 20 parts of water and three times with 12 parts of 2-propanone
  12. customcrystallized from 1,2-dichloroethane
  13. filtrationThe product was filtered off
  14. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-916348cbfc454d67894c8a2b1ce127ac
Source dataset
uspto-grants-1991_01
Patent number
US04988689

Reaction notes

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