4-Aminophenol → HCID 66637003, compound

HRID 469211Notes

Reaction equation

HRID 469211 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:15]1([NH:21][C:22]2[CH:31]=[C:30]3[C:25]([C:26](=[O:39])[C:27]([CH:37]=O)=[CH:28][N:29]3[CH:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:24][C:23]=2[F:40])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[NH2:41][C:42]1[CH:47]=[CH:46][C:45]([OH:48])=[CH:44][CH:43]=1.C(=O)([O-])O.[Na+]>C(O)(=O)C.ClCCCl>[CH:15]1([NH:21][C:22]2[CH:31]=[C:30]3[C:25]([C:26](=[O:39])[C:27]([CH2:37][NH:41][C:42]4[CH:47]=[CH:46][C:45]([OH:48])=[CH:44][CH:43]=4)=[CH:28][N:29]3[CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36]3)=[CH:24][C:23]=2[F:40])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

7

Reactant 4

HCID 4034-AminophenolHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 866330517-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carbaldehyde

Product 1

HCID 66637003HCID 66637003, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

169 mg of sodium triacetoxyborohydride was added to a mixed solution 10 ml of 1,2-dichloroethane and 0.05 ml of acetic acid of 142 mg 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carbaldehyde and 66 mg of 4-aminophenol, followed by stirring for 24 hours. Aqueous saturated sodium hydrogen carbonate was added thereto, followed by extraction with chloroform. After drying over anhydrous sodium sulfate and subsequent filtration, concentration under a reduced pressure was carried out. The resulting residue was purified by silica gel column chromatography and then crystallized from ethyl acetate to obtain 46 mg of [7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-{[(4-hydroxyphenyl)amino]methyl}quinolin-4(1H)-one.

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialAfter drying over anhydrous sodium sulfate and subsequent filtration, concentration under a reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography
  4. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d8b919b9183b4fdf8b645538a4676fd3
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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