Ammonia → HCID 131716774, compound

HRID 1460546Notes

Reaction equation

HRID 1460546 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[NH:7]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15]2[N:23]([CH2:24][C:25]3[O:26][C:27]([CH3:30])=[CH:28][CH:29]=3)[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[N:16]=2)[CH2:9][CH2:8]1.N>CO>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH:2]1([N:7]2[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15]3[N:23]([CH2:24][C:25]4[O:26][C:27]([CH3:30])=[CH:28][CH:29]=4)[C:18]4=[N:19][CH:20]=[CH:21][CH:22]=[C:17]4[N:16]=3)[CH2:9][CH2:8]2)[CH2:1][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 131716775HCID 131716775, compound

Product 1

HCID 131716774HCID 131716774, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6 parts of N-(hexahydro-1H-azepin-4-yl)-3-[(5-methyl-2-furanyl)methyl]-3H-imidazo[4,5-b]-pyridin-2-amine ethanedioate(1:2) and 64 parts of methanol, saturated with ammonia was stirred for 5 minutes at reflux temperature. After cooling, the precipitate was filtered off and the filtrate was evaporated. A mixture of the residue, 5 parts of cyclohexanone, 1 part of a solution of thiophene in methanol 4% and 120 parts of methanol was hydrogenated at normal pressure and at room temperature with 1 part 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 converted into the ethanedioate salt in a small amount of 2-propanone and ethanol. After cooling, the salt was filtered off and crystallized from ethanol. The product was filtered off and dried, yielding 2 parts (23.9%) of N-(1-cyclohexylhexahydro-1H-azepin-4-yl)-3-[(5-methyl-2-furanyl)methyl]-3 H-imidazo[4,5-b]pyridin-2-amine ethanedioate(1:2), hemihydrate; mp. 136.1° C. (compound 206).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationthe precipitate was filtered off
  4. customthe filtrate was evaporated
  5. additionA mixture of the residue, 5 parts of cyclohexanone, 1 part of a solution of thiophene in methanol 4% and 120 parts of methanol
  6. customwas hydrogenated at normal pressure and at room temperature with 1 part of palladium-on-charcoal catalyst 10%
  7. filtrationthe catalyst was filtered off
  8. customthe filtrate was evaporated
  9. temperatureAfter cooling
  10. filtrationthe salt was filtered off
  11. customcrystallized from ethanol
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-a8553c97b90e4d71b73a73303dfce0f8
Source dataset
uspto-grants-1991_12
Patent number
US05071846

Reaction notes

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