Hydrochloride methanol → 5-[3-(Amino)propylamino]imidazo[1,2-a]pyridine dihydrochloride

HRID 5434

Reaction equation

HRID 5434 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[N:18]2[CH:19]=[CH:20][N:21]=[C:17]2[CH:16]=[CH:15][CH:14]=1)=O)(C)(C)C.[ClH:22].CO>C(Cl)Cl>[ClH:22].[ClH:22].[NH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[N:18]2[CH:19]=[CH:20][N:21]=[C:17]2[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 23362879Carbamic acid,[3-(imidazo[1,2-a]pyridin-5-ylamino)propyl]-,1,1-dimethylethyl ester

Product 1

HCID 200866655-[3-(Amino)propylamino]imidazo[1,2-a]pyridine dihydrochlorideYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-[3-(tert-butoxycarbonylamino)propylamino]imidazo[1,2-a]pyridine (1.742 g, 6 mmoles) in methylene chloride (40 ml) was added hydrogen chloride-methanol (6 ml) and the mixture was stirred at room temperature for 20 hours. After the solvent was distilled off, ethanol (15 ml) and ether (30 ml) were added to the residue. Then, the crystals precipitated were filtered off and washed in turn with ether and a small amount of ethanol to obtain 1.311 g of the desired product (83.0%, pale yellow crystals).

Workup

  1. distillationAfter the solvent was distilled off
  2. additionethanol (15 ml) and ether (30 ml) were added to the residue
  3. customThen, the crystals precipitated
  4. filtrationwere filtered off
  5. washwashed in turn with ether

Sources & evidence

ORD record
ord-689b4b2ef67943d4b073104bea7fe4b7
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Linked notes

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