Isopropyl chloroformate → 5-[4-(Isopropyloxycarbonylamino)butylthio]imidazo[1,2-a]pyridine

HRID 1608614Notes

Reaction equation

HRID 1608614 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.Cl[C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25]>C(Cl)Cl>[CH:27]([O:26][C:24]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1)=[O:25])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 233628945-[4-(Amino)butylthio]imidazo[1,2-a]pyridine

Product 1

HCID 233630025-[4-(Isopropyloxycarbonylamino)butylthio]imidazo[1,2-a]pyridineYield 41.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[4-(amino)butylthio]imidazo[1,2-a]pyridine (370 mg, 1.67 mmoles) and triethylamine (0.35 ml, 2.51 mmoles) in metylene chloride (20 ml) was added isopropyl chloroformate (0.25 g, 2.04 mmoles) under ice-cooling with stirring and the mixture was stirred under ice-cooling for 1 hour. The reaction mixture was washed in turn with an aqueous sodium bicarbonate solution and saturated saline and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent: ethyl acetate) to obtain 215 mg of the desired product (41.8%, light tan oily product).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling for 1 hour
  4. washThe reaction mixture was washed in turn with an aqueous sodium bicarbonate solution and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter the solvent was distilled off
  7. customthe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-58772ec7832a4ddd9fe0d8fcff664b9b
Source dataset
uspto-grants-1995_03
Patent number
US05395839

Reaction notes

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