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

HRID 2351736Notes

Reaction equation

HRID 2351736 reaction equation
[CH3:1][CH:2]([N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=[CH:7]1)[C:3]([NH2:5])=[O:4].[ClH:15].C(O[CH:20]([CH3:22])[CH3:21])(C)C>C(O)(C)C>[OH2:4].[ClH:15].[Cl:15][C:21]1[CH:20]=[CH:22][C:14]([C:7]2[N:6]([C@@H:2]([CH3:1])[C:3]([NH:5][CH2:1][CH2:2][N:6]([CH3:10])[CH3:7])=[O:4])[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[N:8]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 86743439alpha-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 hydrate

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-baf7a795f37f432a93fbe799d437b74d
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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