Water → HCID 59529934, compound

HRID 1894949Notes

Reaction equation

HRID 1894949 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][C:20]([CH3:23])([OH:22])[CH3:21])[CH2:15][CH2:14]1)=[O:12])=[CH:5]2.[C:24](OC(=O)C)(=[O:26])[CH3:25].O>O1CCOCC1.C1COCC1>[OH:22][C:20]([CH3:23])([CH3:21])[CH2:19][CH:16]1[CH2:17][CH2:18][N:13]([C:11]([C:6]2[NH:7][C:8]3[C:4]([CH:5]=2)=[CH:3][C:2]([NH:1][C:24](=[O:26])[CH3:25])=[CH:10][CH:9]=3)=[O:12])[CH2:14][CH2:15]1

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 59529905HCID 59529905, compound

Product 1

HCID 59529934HCID 59529934, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 105 mg of 1-{1-[(5-amino-1H-indol-2-yl)carbonyl]piperidin-4-yl}-2-methylpropan-2-ol in 2 mL of dioxane and 2 mL of THF was added 32 μL of acetic anhydride, followed by stirring at room temperature for 2 hours. Water was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography [chloroform:methanol=1:0-10:1], and then solidified using ethyl acetate-hexane to obtain 110 mg of N-(2-{[4-(2-hydroxy-2-methylpropyl)piperidin-1-yl]carbonyl}-1H-indol-5-yl) acetamide as a white solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography [chloroform:methanol=1:0-10:1]

Sources & evidence

ORD record
ord-944d0fc3b9284ed8aac14e666abf821b
Source dataset
uspto-grants-2013_08
Patent number
US08513422B2

Reaction notes

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