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Ammonium Chloride → HCID 19434969, compound

HRID 1736128
Notes
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Reaction equation

HRID 1736128 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:21]([F:22])=[CH:20][C:19]([F:23])=[C:18]([NH2:24])[C:14]=3[C:15](=[O:17])[CH:16]=2)=[CH:7][C:6]=1[F:25])(=[O:3])[CH3:2].CC(C)([O-])C.[K+].Br[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].[Cl-].[NH4+]>CN(C)C=O>[C:1]([N:4]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:21]([F:22])=[CH:20][C:19]([F:23])=[C:18]([NH2:24])[C:14]=3[C:15](=[O:17])[CH:16]=2)=[CH:7][C:6]=1[F:25])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 117544Ethyl 6-bromohexanoateHCID 194349072-(4-Acetylamino-3-fluorophenyl)-5-amino-6,8-difluoro-4H-1-benzopyran-4-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 19434969HCID 19434969, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

1.00 g (2.87 mmol) of Compound 27 obtained in Example 27 was dissolved in 10 ml of dimethylformamide under argon atmosphere, 355 mg of potassium tert-butoxide and 1.02 ml of ethyl 6-bromohexanoate were added under ice-cooling and the mixture was stirred at room temperature for 4.5 hours. An aqueous ammonium chloride solution was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride, dried over anhydrous sodium sulfate and purified by silica gel column chromatography (chloroform:methanol=30:1) to give 1.26 g (85%) of 2-[4-[N-acetyl-N-(5-ethoxycarbonylpentyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. custompurified by silica gel column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-f824ce49ef8a4e65b38cfd652b8fdd45
Source dataset
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05539112

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes