Hydrochloric Acid → (S)-2-(4-Chlorophenyl)-N-[2-(dimethylamino)ethyl]-alpha-methyl-3H-imidazo[4,5-b]pyridine-3-acetamide hydrochloride hydrate

HRID 1709552Notes

Reaction equation

HRID 1709552 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([C@@H:17]([CH3:26])[C:18]([NH:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.Cl.C(OC(C)C)(C)C>C(O)(C)C>[OH2:19].[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([C@@H:17]([CH3:26])[C:18]([NH:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 14390415(S)-2-(4-Chlorophenyl)-N-[2-(dimethylamino)ethyl]-alpha-methyl-3H-imidazo [4,5-b]pyridine-3-acetamide

Product 1

HCID 70356911(S)-2-(4-Chlorophenyl)-N-[2-(dimethylamino)ethyl]-alpha-methyl-3H-imidazo[4,5-b]pyridine-3-acetamide hydrochloride hydrateYield 229.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of crude (S)-2-(4-chlorophenyl)-N-[2-(dimethylamino)ethyl]-α-methyl-3H-imidazo[4,5-b]pyridine-3-acetamide (1.49 g, 0.00335 mole) in hot isopropyl alcohol was treated with hydrogen chloride in isopropyl alcohol until the solution was acidic. Upon addition of isopropyl ether, solid precipitated. After cooling to room temperature, the solid was collect by filtration, rinsed with isopropyl ether, an dried under high vacuum to give 1.64 g of title compound, mp 252°-255° C.

Workup

  1. customprecipitated
  2. filtrationthe solid was collect by filtration
  3. washrinsed with isopropyl ether
  4. customan dried under high vacuum

Sources & evidence

ORD record
ord-c99d72606b6b4f06b03fb21d81ebb0d0
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

Loading…