Acetic Acid → HCID 59529896, compound

HRID 1894950Notes

Reaction equation

HRID 1894950 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.CO[CH:26]1[CH2:30][CH2:29][CH:28](OC)O1.C(O)(=O)C.Cl>CO>[CH3:21][C:20]([OH:22])([CH3:23])[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]([N:1]2[CH:26]=[CH:30][CH:29]=[CH:28]2)=[CH:10][CH:9]=3)=[O:12])[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 790982,5-DimethoxytetrahydrofuranHCID 59529905HCID 59529905, compound

Product 1

HCID 59529896HCID 59529896, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 127 mg of 1-{1-[(5-amino-1H-indol-2-yl)carbonyl]piperidin-4-yl}-2-methylpropan-2-ol in 3 mL of methanol were added 90 μl, of 2,5-dimethoxytetrahydrofuran and 1 mL of acetic acid, followed by stirring at 60° C. for 1 day. 1M hydrochloric acid was added to the reaction liquid which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous 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 from ethyl acetate-hexane to obtain 30 mg of 2-methyl-1-(1-{[5-(1H-pyrrol-1-yl)-1H-indol-2-yl]carbonyl}piperidin-4-yl)propan-2-ol as a white solid.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous 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-591760d8a363479496364e0b1b34f588
Source dataset
uspto-grants-2013_08
Patent number
US08513422B2

Reaction notes

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