Hydrochloric Acid → HCID 21913356, compound

HRID 1245997Notes

Reaction equation

HRID 1245997 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-69106c5471174f19a520afe4ab39d779
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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