Hydrochloric Acid → 2-(4-Bromophenyl)-N-[4-(dimethylamino)phenyl]-3H-imidazo [4,5-b]pyridine-3-acetamide hydrochloride hydrate

HRID 623040Notes

Reaction equation

HRID 623040 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([N:27]([CH3:29])[CH3:28])=[CH:23][CH:22]=3)=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[ClH:30]>C(#N)C>[OH2:19].[ClH:30].[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:20][C:21]3[CH:22]=[CH:23][C:24]([N:27]([CH3:29])[CH3:28])=[CH:25][CH:26]=3)=[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14390313HCID 14390313, compound

Product 1

HCID 230373842-(4-Bromophenyl)-N-[4-(dimethylamino)phenyl]-3H-imidazo [4,5-b]pyridine-3-acetamide hydrochloride hydrateYield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 0.7-g sample (0.00155 mole) of 2-(4-bromophenyl)-N-[4-(dimethylamino)phenyl]-3H-imidazo[4,5-b]pyridine-3-acetamide obtained in Example 244, was dissolved in acetonitrile (150 ml), acidified with ethereal hydrogen chloride, and refrigerated overnight with seeding. The solid was collected by filtration, washed with diethyl ether-acetonitrile, and dried under high vacuum overnight. The solid was sublimed under high vacuum at 70° C. to give 0.47 g (55%) of title compound, 180° C. (effervescence).

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with diethyl ether-acetonitrile
  3. customdried under high vacuum overnight
  4. customwas sublimed under high vacuum at 70° C.

Sources & evidence

ORD record
ord-6c96f1a559914325b0350b0beb78fad8
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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