1-Hydroxybenzotriazole → HCID 86682827, compound

HRID 1428181Notes

Reaction equation

HRID 1428181 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([OH:18])=O)=[CH:4][CH:3]=1.[CH3:19][S:20]([CH2:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)(=[O:22])=[O:21].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>O.CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:28][C:27]2[CH:29]=[CH:30][C:24]([CH2:23][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:25][CH:26]=2)=[O:18])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 128439644-[(methylsulfonyl)methyl]aniline(SALTDATA: FREE)HCID 86682820HCID 86682820, compound

Product 1

HCID 86682827HCID 86682827, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (2E)-3-[4-(4-fluorophenyl)pyridin-3-yl]prop-2-enoic acid (0.24 g), 4-[(methylsulfonyl)methyl]aniline (0.19 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.25 g), 1-hydroxy-1H-1,2,3-benzotriazole (0.20 g) and N,N-dimethylformamide (10 mL) was stirred at room temperature for 15 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to give a solid. The obtained solid was recrystallized from acetone/hexane to give the title compound (0.28 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customto give a solid
  6. customThe obtained solid was recrystallized from acetone/hexane

Sources & evidence

ORD record
ord-d03a678e789948c69fb63ea6f8ae0e19
Source dataset
uspto-grants-2015_01
Patent number
US08937055B2

Reaction notes

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