Tetrahydrofuran → HCID 66637045, compound

HRID 469240Notes

Reaction equation

HRID 469240 reaction equation
C1COCC1.[Si]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][C:23]([NH:30][CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[C:24]([F:29])[CH:25]=2)[N:20]([CH:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)[CH:19]=1)(C(C)(C)C)(C)C>O>[CH:31]1([NH:30][C:23]2[CH:22]=[C:21]3[C:26]([C:27](=[O:28])[C:18]([O:17][CH2:16][CH2:15][CH2:14][OH:13])=[CH:19][N:20]3[CH:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)=[CH:25][C:24]=2[F:29])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 66636801HCID 66636801, compound

Product 1

HCID 66637045HCID 66637045, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 15 ml THF solution of 762 mg of 3-(3-{[tert-butyl(dimethyl)silyl]oxy}propoxy)-7-(cyclohexylamino)-1-cyclopentyl-6-fluoroquinolin-4(1H)-one was added 1.5 ml of a 1 M tetrabutylammonium fluoride THF solution at room temperature, followed by stirring for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate and washing with aqueous saturated sodium chloride. After drying over anhydrous sodium sulfate, evaporation was carried out under a reduced pressure. By purifying the residue by silica gel column chromatography, 273 mg of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-(3-hydroxypropoxy)quinolin-4(1H)-one was obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washwashing with aqueous saturated sodium chloride
  3. dry with materialAfter drying over anhydrous sodium sulfate, evaporation
  4. customBy purifying the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-54c5cb9d840f438797b41b1a63159fc2
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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