HCID 86590769, compound → HCID 21913544, compound

HRID 1352645Notes

Reaction equation

HRID 1352645 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][N:13]1[C:21]2[C:20]([CH3:22])=[C:19]([Cl:23])[N:18]=[C:17]([N:24](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)[C:16]=2[N:15]=[C:14]1[CH2:43][CH2:44][CH3:45])(C)(C)C>FC(F)(F)C(O)=O>[NH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][N:13]1[C:21]2[C:20]([CH3:22])=[C:19]([Cl:23])[N:18]=[C:17]([NH2:24])[C:16]=2[N:15]=[C:14]1[CH2:43][CH2:44][CH3:45]

Participants

3

Reactant 1

HCID 86590769HCID 86590769, compound

Product 1

HCID 21913544HCID 21913544, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid (40 mL) was added to [2-(2-{4-[bis-(4-methoxybenzyl)amino]-6-chloro-7-methyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl}ethoxy)ethyl]carbamic acid tert-butyl ester (1 g, 1.5 mmol). The reaction was swirled until it became homogeneous and was allowed to stand at room temperature overnight. The reaction was concentrated under reduced pressure, and dichloromethane was added and removed under reduced pressure (5×40 mL) to provide a white solid. The solid was triturated in chloroform, isolated by filtration, and dried under reduced pressure with heating. The solid was dissolved in concentrated hydrochloric acid (5 mL) and stirred for three hours. Aqueous sodium hydroxide was then added. A white solid formed, which was isolated by filtration, washed with water and diethyl ether, and dried for five hours under high vacuum at 70° C. to provide 0.144 g of 1-[2-(2-aminoethoxy)ethyl]-6-chloro-7-methyl-2-propyl-1H-imidazo[4,5-c]pyridin-4-amine as a white solid, mp 158.0–161.0° C.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure, and dichloromethane
  2. additionwas added
  3. customremoved under reduced pressure (5×40 mL)
  4. customto provide a white solid
  5. customThe solid was triturated in chloroform
  6. customisolated by filtration
  7. customdried under reduced pressure
  8. temperaturewith heating
  9. dissolutionThe solid was dissolved in concentrated hydrochloric acid (5 mL)
  10. additionAqueous sodium hydroxide was then added
  11. customA white solid formed
  12. customwhich was isolated by filtration
  13. washwashed with water and diethyl ether
  14. customdried for five hours under high vacuum at 70° C.

Sources & evidence

ORD record
ord-510f59d779024743a3acd2aea6450ab3
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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