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Water → 1-(4-Hydroxyphenyl)cyclopropanecarboxylic Acid {4-[3-(acetylmethylamino)pyrrolidin-1-yl]phenyl}amide

HRID 2426642
Notes
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Reaction equation

HRID 2426642 reaction equation
B(Br)(Br)Br.CSC.[C:8]([CH2:11][NH:12][CH:13]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]3([C:30]4[CH:35]=[CH:34][C:33]([O:36]C)=[CH:32][CH:31]=4)[CH2:29][CH2:28]3)=[O:26])=[CH:20][CH:19]=2)[CH2:14]1)(=[O:10])[CH3:9].O>ClCCl>[C:8]([CH2:11][NH:12][CH:13]1[CH2:17][CH2:16][N:15]([C:18]2[CH:19]=[CH:20][C:21]([NH:24][C:25]([C:27]3([C:30]4[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=4)[CH2:28][CH2:29]3)=[O:26])=[CH:22][CH:23]=2)[CH2:14]1)(=[O:10])[CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 10946916Boron tribromide methyl sulfideHCID 86594872HCID 86594872, compound

Product 1

HCID 865948711-(4-Hydroxyphenyl)cyclopropanecarboxylic Acid {4-[3-(acetylmethylamino)pyrrolidin-1-yl]phenyl}amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide-dimethyl sulfide (460 mg) was added to a solution of 1-(4-methoxyphenyl)cyclopropanecarboxylic acid {4-[3-(acetylmethylamino)pyrrolidin-1-yl]phenyl}amide (540 mg) in dichloromethane (5.5 ml) at 0° C. After a reaction time of 12 hours at room temperature, water was added to the mixture, the phases were separated, and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, concentrated and purified by chromatography (silica gel, toluene/ethanol/ethyl acetate 8:1:1 with addition of 0.1% triethylamine). This resulted in the product with the molecular weight of 393.49 (C23H27N3O3); MS(ESI): 394 (M+H+).

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by chromatography (silica gel, toluene/ethanol/ethyl acetate 8:1:1 with addition of 0.1% triethylamine)
  6. customThis resulted in the product with the molecular weight of 393.49 (C23H27N3O3)

Sources & evidence

ORD record
ord-550304888d0645dc881be2f53b6e30be
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07968550B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes