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

HRID 1081759Notes

Reaction equation

HRID 1081759 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 5-(4-amino)butylthioimidazo[1,2-a]pyridine (370 mg, 1.67 mmoles) and triethylamine (0.35 ml, 2.51 mmoles) in methylene 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 aqueous saturated sodium bicarbonate and saturated saline, and then 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 aqueous saturated sodium bicarbonate 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-211dfeb751824b05ab69a08afa7c5a09
Source dataset
uspto-grants-1996_12
Patent number
US05587383

Reaction notes

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