Hydrochloric Acid → HCID 21913356, compound

HRID 1008104Notes

Reaction equation

HRID 1008104 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-2da1dcdd82d140a18c3bbde3e748347d
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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