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

HRID 2073064Notes

Reaction equation

HRID 2073064 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 collected by filtration, rinsed with isopropyl ether, and dried under high vacuum to give 1.64 g of title compound, mp 252°-255° C.

Workup

  1. customprecipitated
  2. filtrationthe solid was collected by filtration
  3. washrinsed with isopropyl ether
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-d5467264d1364cdcbfa3c09c8bf4d0f0
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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