1-Hydroxybenzotriazole → (5-(4-Chlorophenyl)isoxazol-4-yl)(3-(pyridin-3-yl)pyrrolidin-1-yl)methanone

HRID 1446150Notes

Reaction equation

HRID 1446150 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[CH2:2]1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:23][N:22]=[CH:21][C:20]=2[C:24](O)=[O:25])=[CH:15][CH:14]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN1CCCC1=O.O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[O:23][N:22]=[CH:21][C:20]=2[C:24]([N:1]2[CH2:5][CH2:4][CH:3]([C:6]3[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=3)[CH2:2]2)=[O:25])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 36136513-(Pyrrolidin-3-yl)pyridineHCID 228316965-(4-Chlorophenyl)-1,2-oxazole-4-carboxylic acid

Product 1

HCID 59170218(5-(4-Chlorophenyl)isoxazol-4-yl)(3-(pyridin-3-yl)pyrrolidin-1-yl)methanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a 150 mL round-bottomed flask equipped with magnetic stirring was added 3-(pyrrolidin-3-yl)pyridine (1.0 g, 6.7 mmol, source: ASDI Inc.) in 25 mL of N-methylpyrrolidinone (NMP). To this solution was added 5-(4-chlorophenyl)isoxazole-4-carboxylic acid (1.6 g, 7.1 mmol, source: CiVentiChem), 1-hydroxybenzotriazole (1.0 g, 7.4 mmol), and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (1.6 g, 8.1 mmol), and the mixture was stirred at ambient temp. After ca. 4 days, water was added (ca. 150 mL) and the aqueous layer was extracted with EtOAc (3×75 mL). The organic extracts were combined, washed with water, sat'd NaHCO3, and brine. The organic layers were combined and dried over MgSO4, filtered and concentrated in vacuo. The crude material was absorbed onto silica gel and purified on a 120 g Isco Redi-sep® silica gel column using CH2Cl2 with 3% (2M NH3 in CH3OH) as the eluant to give the desired product. Mass Spec. m/z+ion=354.1, m/z negative ion=352.1.

Workup

  1. customTo a 150 mL round-bottomed flask equipped
  2. stirringthe mixture was stirred at ambient temp
  3. extractionthe aqueous layer was extracted with EtOAc (3×75 mL)
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was absorbed onto silica gel
  9. custompurified on a 120 g Isco Redi-sep® silica gel column

Sources & evidence

ORD record
ord-60a0cdbc9c7547959dd5f3eca266432a
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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