Acetic Acid → HCID 90026322, compound

HRID 873753Notes

Reaction equation

HRID 873753 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([C:10]3[CH:11]=[C:12]4[C:25]5([CH2:29][O:28][C:27]([NH2:30])=[N:26]5)[C:21]5([CH2:24][O:23][CH2:22]5)[C:17]5([CH2:20][CH2:19][CH2:18]5)[O:16][C:13]4=[CH:14][CH:15]=3)=[CH:6][N:5]2[CH:31]=1.C(O)(=O)C.[H][H]>CCO.O=[Pt]=O>[CH3:1][C:2]1[N:3]=[C:4]2[CH2:9][CH2:8][CH:7]([C:10]3[CH:11]=[C:12]4[C:25]5([CH2:29][O:28][C:27]([NH2:30])=[N:26]5)[C:21]5([CH2:24][O:23][CH2:22]5)[C:17]5([CH2:18][CH2:19][CH2:20]5)[O:16][C:13]4=[CH:14][CH:15]=3)[CH2:6][N:5]2[CH:31]=1

Participants

6

Reactant 3

HCID 176Acetic Acid2×HCID 90017611HCID 90017611, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 90026322HCID 90026322, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A suspension of 6′-(2-methylimidazo[1,2-a]pyridin-6-yl)trispiro[cyclobutane-1,2′-chromene-4′,4″-[1,3]oxazole-3′,3′″-oxetan]-2″-amine (66 mg, 0.16 mmol), acetic acid (27 μl, 0.06 mmol) and PtO2 (13 mg) in EtOH (3.3 ml) was stirred at room temperature under the hydrogen atmosphere at 3 atm for 8 hours. To the mixture was added acetic acid (63 μl), and the mixture was stirred at room temperature under hydrogen atmosphere at 3 atm for 38 hours. The mixture was filtrated through celite pad. And then the filtrate was concentrated under reduced pressure. The obtained residue was purified by silicagel column chromatography (28% NH4OH/EtOH/CHCl3=2:20:80) followed by trituration in iPr2O and filtration to give 6′-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-yl)trispiro[cyclobutane-1,2′-chromene-4′,4″-[1,3]oxazole-3′,3′″-oxetan]-2″-amine (56 mg).

Workup

  1. filtrationThe mixture was filtrated through celite pad
  2. concentrationAnd then the filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silicagel column chromatography (28% NH4OH/EtOH/CHCl3=2:20:80)
  4. filtrationfiltration

Sources & evidence

ORD record
ord-fa824c1ffc1b4b3a90256a54184b3735
Source dataset
uspto-grants-2015_03
Patent number
US08975415B2

Reaction notes

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