Acetic Acid → HCID 59540815, compound

HRID 1677408Notes

Reaction equation

HRID 1677408 reaction equation
[CH3:1][C:2]([O:27]C1CCCCO1)([CH3:26])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[N:12]=2)[NH:7][CH:6]=1)=[O:4].C(O)(=O)C.C1COCC1>O>[OH:27][C:2]([CH3:26])([CH3:1])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:14]3[CH:15]=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=3)[N:12]=2)[NH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 59540682HCID 59540682, compound

Product 1

HCID 59540815HCID 59540815, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

2-Methyl-2-(tetrahydro-pyran-2-yloxy)-1-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one, 0.012 gm, was mixed with 0.8 ml acetic acid, 0.4 ml THF and 0.2 ml water and heated for 90 minutes in a 50° C. oil bath. The mixture was concentrated, saturated aqueous sodium bicarbonate was added and the mixture extracted twice with ethyl acetate, dried over magnesium sulfate, filtered and stripped and the solid dried overnight at 2 torr in an 80° C. vacuum oven to give 2-Hydroxy-2-methyl-1-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one. (M+H)+=372.

Workup

  1. concentrationThe mixture was concentrated
  2. additionsaturated aqueous sodium bicarbonate was added
  3. extractionthe mixture extracted twice with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solid dried overnight at 2 torr in an 80° C. vacuum oven

Sources & evidence

ORD record
ord-613dc7499d07468383458b15040e0d46
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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