Ammonium Chloride → HCID 66636981, compound

HRID 469251Notes

Reaction equation

HRID 469251 reaction equation
[Br-].[CH2:2]([O:9][CH2:10][CH2:11][CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[K].CC(C)([O-])C.[CH:38]1([NH:44][C:45]2[CH:54]=[C:53]3[C:48]([C:49](=[O:62])[C:50]([CH:60]=O)=[CH:51][N:52]3[CH:55]([CH2:58][CH3:59])[CH2:56][CH3:57])=[CH:47][C:46]=2[F:63])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1.[Cl-].[NH4+]>C1COCC1>[CH2:2]([O:9][CH2:10][CH2:11][CH:12]=[CH:60][C:50]1[C:49](=[O:62])[C:48]2[C:53](=[CH:54][C:45]([NH:44][CH:38]3[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]3)=[C:46]([F:63])[CH:47]=2)[N:52]([CH:55]([CH2:56][CH3:57])[CH2:58][CH3:59])[CH:51]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 45749132-Methylpropan-2-olateHCID 5462222PotassiumHCID 10929077(3-Benzyloxypropyl)triphenylphosphonium bromideHCID 86633064HCID 86633064, compound

Product 1

HCID 66636981HCID 66636981, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 20 ml THF suspension of 1081 mg of (3-benzyloxypropyl)triphenylphosphonium bromide was added 258 mg of potassium, tert-butoxide followed by stirring for 1.5 hours. A 10 ml THF solution of 358 mg of 7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carbaldehyde was added thereto, followed by stirring for 1 hour. To the reaction mixture was added aqueous saturated ammonium chloride, followed by extraction with ethyl acetate and washing with aqueous saturated sodium chloride. After drying over anhydrous sodium sulfate and subsequent concentration under a reduced pressure, the residue was purified by silica gel column chromatography to obtain 488 mg of 3-[4-(benzyloxy)but-1-en-1-yl]-7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoroquinolin-4(1H)-one.

Workup

  1. stirringby stirring for 1 hour
  2. extractionfollowed by extraction with ethyl acetate
  3. washwashing with aqueous saturated sodium chloride
  4. dry with materialAfter drying over anhydrous sodium sulfate and subsequent concentration under a reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f386f690384a4225b083ba4e5a95032f
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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