1,2-Dichloroethane → HCID 57465130, compound

HRID 1170871Notes

Reaction equation

HRID 1170871 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]2=[N:8][C:7]=1[NH2:15])=[O:5])[CH3:2].C(O[BH-](O[C:26](=O)[CH3:27])OC(=O)C)(=O)C.[Na+].Cl[CH2:31][CH2:32]Cl>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]2=[N:8][C:7]=1[NH:15][CH2:31][CH2:32][CH2:26][CH3:27])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 5200237Ethyl 2-amino-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 57465130HCID 57465130, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound E was dissolved in DCE (150 mL) and n-butylaldehyde (49.7 mmol, 4.4 mL, 1.5 eq.) was added thereto. Sodium triacetoxyborohydride (11.93 g, 56.3 mmol, 1.7 eq.) was then gradually added and the reaction mixture was stirred for four hours at room temperature. The reaction mixture was diluted with DCM (500 ml) and washed with saturated aqueous NaHCO3 solution (500 mL). The aqueous phases were extracted with DCM (100 mL) and the combined organic phases were washed with saturated aqueous NaCl solution (500 mL), dried over sodium sulphate and the solvent was removed under vacuum. The untreated product was purified by means of column chromatography (SiO2, heptane/EtOAc 4:1→3:1) and 5.7 g (65%) of the desired product 2-butylamino-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester (F) were obtained.

Workup

  1. washwashed with saturated aqueous NaHCO3 solution (500 mL)
  2. extractionThe aqueous phases were extracted with DCM (100 mL)
  3. washthe combined organic phases were washed with saturated aqueous NaCl solution (500 mL)
  4. dry with materialdried over sodium sulphate
  5. customthe solvent was removed under vacuum
  6. customThe untreated product was purified by means of column chromatography (SiO2, heptane/EtOAc 4:1→3:1)

Sources & evidence

ORD record
ord-cf74f5b9e47b4f8885f29ac783f79750
Source dataset
uspto-grants-2010_11
Patent number
US07829568B2

Reaction notes

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