Acetic Acid → HCID 14368386, compound

HRID 1762214Notes

Reaction equation

HRID 1762214 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([O:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[NH:19][C:20](=[O:24])[C:21]([CH3:23])=[O:22])=[CH:8][CH:7]=[CH:6][N:5]2[C:25]=1[CH2:26][C:27]#[CH:28].C(O)(=O)C.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>C(O)C>[C:20]([NH:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[C:12]=1[CH2:11][O:10][C:9]1[C:4]2[N:5]([C:25]([CH2:26][C:27]#[CH:28])=[C:2]([CH3:1])[N:3]=2)[CH:6]=[CH:7][CH:8]=1)(=[O:24])[CH:21]([CH3:23])[OH:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 14368378HCID 14368378, compound

Product 1

HCID 14368386HCID 14368386, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-methyl-3-(2-propynyl)-8-(2-pyruvamido-6-methylbenzyloxy)imidazo[1,2-a]pyridine (287 mg) in the mixture of acetic acid (0.13 ml) and ethanol (3 ml), sodium cyanoborohydride (72 mg) was added portionwise for 2.5 hours at 5° C. The mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate and extracted with chloroform. The extract was washed with water, dried over magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel (10 g) and eluted with a mixture of chloroform and methanol (100.1) to give 8-(2-lactamido-6-methylbenzyloxy)-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine (138 mg).

Workup

  1. additionwas added portionwise for 2.5 hours at 5° C
  2. extractionextracted with chloroform
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washeluted with a mixture of chloroform and methanol (100.1)

Sources & evidence

ORD record
ord-f97f7adc85614df490c4ee027415db49
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

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