Hydrochloric Acid → HCID 86612259, compound

HRID 1623146Notes

Reaction equation

HRID 1623146 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]=[C:9]([CH2:31][CH2:32][CH3:33])[N:10]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]([O:23]C(OC(C)(C)C)=O)C(=O)OC(C)(C)C)[C:6]=2[C:5]([CH3:34])=[C:4]([CH3:35])[N:3]=1.Cl.O1CCOCC1>ClCCl>[NH2:1][C:2]1[C:7]2[N:8]=[C:9]([CH2:31][CH2:32][CH3:33])[N:10]([CH2:11][CH2:12][CH2:13][CH2:14][NH:15][OH:23])[C:6]=2[C:5]([CH3:34])=[C:4]([CH3:35])[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86612256HCID 86612256, compound2×

Product 1

HCID 86612259HCID 86612259, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The preparation of tert-butyl 4-(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl[(tert-butoxycarbonyl)oxy]carbamate is described in Parts A-F of Example 14. A mixture of 4M hydrochloric acid in dioxane (2.25 mL, 9.0 mmol, 20 eq) was added to a solution of tert-butyl 4-(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl[(tert-butoxycarbonyl)oxy]carbamate (0.22 g, 0.45 mmol, 1 eq) in dichloromethane (5 mL) and stirred for 2 hours. The reaction mixture was concentrated under reduced pressure and the resulting white solid was concentrated from chloroform and dried under vacuum to provide N-[4-(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]hydroxylamine.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationthe resulting white solid was concentrated from chloroform
  3. customdried under vacuum

Sources & evidence

ORD record
ord-c013e6ce88d14abfb6b5e0c67965c99a
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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