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

HRID 623079
Notes
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Reaction equation

HRID 623079 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 3776
Isopropanol
Solvent
2×

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-b6aeaa06897b4c8cb32281196cb14c70
Source dataset
uspto-grants-1988_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04772600

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes