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Hydrochloric Acid → 6-Cyano-imidazo[1,2-a]pyridine-2-carboxylic acid-(4-dipropylamino-butyl)-amide

HRID 2080773
Notes
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Reaction equation

HRID 2080773 reaction equation
[CH2:1]([N:4]([CH2:10][CH2:11][CH3:12])[CH2:5][CH2:6][CH2:7][CH2:8][NH2:9])[CH2:2][CH3:3].C[Al](C)C.CCCCCC.C([O:25][C:26]([C:28]1[N:29]=[C:30]2[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][N:31]2[CH:38]=1)=O)C.Cl>ClCCl>[CH2:10]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:26]([C:28]1[N:29]=[C:30]2[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][N:31]2[CH:38]=1)=[O:25])[CH2:11][CH3:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7138396N,N-dipropylbutane-1,4-diamineHCID 10512851Ethyl 6-Cyanoimidazo[1,2-a]pyridine-2-carboxylateHCID 86584505Trimethylaluminum hexane

Product 1

HCID 231554976-Cyano-imidazo[1,2-a]pyridine-2-carboxylic acid-(4-dipropylamino-butyl)-amideYield 49.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (263 mg) obtained in Example 1-2 was dissolved in dichloromethane (4.0 ml) and a 15% trimethyl aluminum/hexane solution (1.08 ml) was dropped thereto. The whole was stirred at room temperature for 15 minutes. The solution was added with the compound (300 mg) obtained in Example 19-1 and stirred for additional 20 hours. The resultant was heated to 40° C. and stirred for additional 7 hours, and then 1 mol/l hydrochloric acid was added to stop the reaction, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, water, and a saturated saline solution and dried with anhydrous sodium sulfate. The residue obtained by distilling the solvent off was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (237 mg) as a yellow solid.

Workup

  1. stirringstirred for additional 20 hours
  2. temperatureThe resultant was heated to 40° C.
  3. stirringstirred for additional 7 hours
  4. customthe reaction
  5. extractionfollowed by extraction with chloroform
  6. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, water
  7. dry with materiala saturated saline solution and dried with anhydrous sodium sulfate
  8. customThe residue obtained
  9. distillationby distilling the solvent
  10. customoff was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-6581db11a1604fd7948f045a190880e1
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07932281B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes