Hydrochloric Acid → HCID 21913356, compound

HRID 1352649Notes

Reaction equation

HRID 1352649 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:17][CH2:18][O:19][CH2:20][C:21]#[C:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH2:15])[C:8]=2[N:16]=1)[CH3:2].[ClH:29]>C(OCC)C>[ClH:29].[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH2:15])[C:8]=2[N:16]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21913161HCID 21913161, compound

Product 1

HCID 21913356HCID 21913356, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The general method described in Example 112 was used to hydrogenate 2-ethoxymethyl-6,7-dimethyl-1-{2-[(3-phenylprop-2-ynyl)oxy]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine (1.17 g, 3.09 mmol), prepared as described in Example 122. The reaction was complete after 18 hours. The crude product, isolated as an oil, was dissolved with diethyl ether (20 mL) and treated with a 1 M solution of hydrochloric acid in diethyl ether. The resulting salt was isolated by filtration, dried under reduced pressure, and recrystallized from ethyl acetate. The crystals, obtained in two crops, were dried for three hours under high vacuum at 60° C. to provide 0.777 g of 2-ethoxymethyl-6,7-dimethyl-1-[2-(3-phenylpropoxy)ethyl]-1H-imidazo[4,5-c]pyridin-4-amine hydrochloride as a white powder, mp 128–130° C.

Workup

  1. customprepared
  2. customThe crude product, isolated as an oil
  3. customThe resulting salt was isolated by filtration
  4. customdried under reduced pressure
  5. customrecrystallized from ethyl acetate
  6. customThe crystals, obtained in two crops
  7. customwere dried for three hours under high vacuum at 60° C.

Sources & evidence

ORD record
ord-c5e1323e97774d7ab1938710c880871a
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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