Ammonium formate → HCID 57515430, compound

HRID 44747Notes

Reaction equation

HRID 44747 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1[C:14]2[N:15]=[C:16]([CH2:26][CH2:27][CH3:28])[N:17]([CH2:18][C:19]3([OH:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:13]=2[C:12]([CH3:29])=[C:11]([CH3:30])[N:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO.C(O)C>[NH2:8][C:9]1[C:14]2[N:15]=[C:16]([CH2:26][CH2:27][CH3:28])[N:17]([CH2:18][C:19]3([OH:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:13]=2[C:12]([CH3:29])=[C:11]([CH3:30])[N:10]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formate2×HCID 57515434HCID 57515434, compound

Product 1

HCID 57515430HCID 57515430, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1-{[4-(dibenzylamino)-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl]methyl}cyclohexanol (1.50 g, 3.02 mmol), ammonium formate (2.84 g, 45.0 mmol), and 10% palladium on carbon (1.50 g) in methanol (60 mL) and ethanol (120 mL) was heated at 85° C. for 2 h. More ammonium formate (1.00 g) was added and heating was continued of 3 h, then the reaction mixture was stirred overnight at rt. The mixture was filtered through CELITE filter agent and the filtrate was concentrated in vacuo. The crude product was purified using HPFC (gradient elution with 10-40% CMA/chloroform). The appropriate fractions were concentrated and the resulting solid was triturated with acetonitrile. A solid was isolated by filtration and dried at 100° C. under vacuum to provide 1-[(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)methyl]cyclohexanol as a white powder (0.61 g, 64%), mp 214.0-216.0° C. Anal. Calcd for C18H28N4O C, 68.32; H, 8.92; N, 17.71. Found: C, 68.06; H, 8.65; N, 17.45

Workup

  1. temperatureheating
  2. filtrationThe mixture was filtered through CELITE
  3. filtrationfilter agent
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe crude product was purified
  6. washHPFC (gradient elution with 10-40% CMA/chloroform)
  7. concentrationThe appropriate fractions were concentrated
  8. customthe resulting solid was triturated with acetonitrile
  9. customA solid was isolated by filtration
  10. customdried at 100° C. under vacuum

Sources & evidence

ORD record
ord-88d0defcd8c5410e8908b5f07c3248d7
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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