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1,1'-Carbonyldiimidazole → 2-(4-Chlorophenyl)-N-[3-(dimethylamino)propyl]-3H-imidazo [4,5-b]pyridine-3-acetamide hydrochloride hydrate

HRID 621924
Notes
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Reaction equation

HRID 621924 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[C:21]([N:28]1[CH:32]=[CH:31]N=[CH:29]1)(N1C=CN=C1)=O.[CH3:33][NH:34]N(CCC)NC>O1CCCC1>[OH2:19].[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:34][CH2:33][CH2:31][CH2:32][N:28]([CH3:21])[CH3:29])=[O:20])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acidHCID 56982963N,N-dimethylaminopropylamine

Product 1

HCID 230373362-(4-Chlorophenyl)-N-[3-(dimethylamino)propyl]-3H-imidazo [4,5-b]pyridine-3-acetamide hydrochloride hydrate

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

Under nitrogen bubbling, a mixture of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0174 mole) and 1,1'-carbonyldiimidazole (2.82 g, 0.0174 mole) in 150 ml of tetrahydrofuran was stirred at room temperature for 3 hrs. Under a nitrogen atmosphere, N,N-dimethylaminopropylamine (1.94 g, 0.019 mole) was added dropwise and the reaction was allowed to stir at room temperature overnight. The tetrahydrofuran was evaporated to dryness and the residue was treated with ice water. The solid was collected by filtration and dried under high vacuum. The solid was dissolved in isopropyl alcohol, acidified with ethereal hydrogen chloride, and seeded. The crystalline material was collected by filtration, washed with cold isopropyl alcohol, and dried under high vacuum at 50° C. over the weekend to give 2.78 g (34.5%), mp. 188°-90° C.

Workup

  1. stirringto stir at room temperature overnight
  2. customThe tetrahydrofuran was evaporated to dryness
  3. additionthe residue was treated with ice water
  4. filtrationThe solid was collected by filtration
  5. customdried under high vacuum
  6. dissolutionThe solid was dissolved in isopropyl alcohol
  7. filtrationThe crystalline material was collected by filtration
  8. washwashed with cold isopropyl alcohol
  9. customdried under high vacuum at 50° C. over the weekend
  10. customto give 2.78 g (34.5%), mp. 188°-90° C.

Sources & evidence

ORD record
ord-e6d28f3205ed4f26a101a1b1d36dd327
Source dataset
uspto-grants-1989_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04824951

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes