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

HRID 1354697Notes

Reaction equation

HRID 1354697 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]

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-c2e7d3df462c405cab93991e775cd406
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

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