1-Hydroxybenzotriazole → HCID 59170262, compound

HRID 1446151Notes

Reaction equation

HRID 1446151 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.[C:12]1([C:18]2[O:22][N:21]=[CH:20][C:19]=2[C:23](O)=[O:24])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O.CN1CCCC1=O>[C:12]1([C:18]2[O:22][N:21]=[CH:20][C:19]=2[C:23]([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:24])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 36136513-(Pyrrolidin-3-yl)pyridineHCID 147872535-Phenylisoxazole-4-carboxylic acid

Product 1

HCID 59170262HCID 59170262, compoundYield 50.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a 15 mL round-bottomed flask equipped with magnetic stirring was added 3-(pyrrolidin-3-yl)pyridine (250 mg, 1700 μmol, source: ASDI Inc.) and 4 mL of N-methylpyrrolidinone (NMP). 5-Phenylisoxazole-4-carboxylic acid (300 mg, 1600 μmol, source: CiVentiChem) was added followed by 1-hydroxybenzotriazole (250 mg, 1800 μmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (380 mg, 2000 μmol). Added 2 mL more NMP, and the reaction mixture was stirred at ambient temp. After 3 days, added 30 mL of water and extracted with EtOAc (3×15 mL). The organic layers were combined, washed with sat'd NaHCO3 and brine. The organic layers were then dried over MgSO4, filtered and concentrated in vacuo. The sample was absorbed onto silica gel and purified on a 40 g Isco Redi-sep® silica gel column that had been pre-equilibrated with CH2Cl2+2% MeOH. The product was eluted sample with CH2Cl2+2% (2M NH3 in MeOH). A viscous yellow oil was isolated as desired product (mass=260 mg). Mass Spec. m/z+ion=320.1.

Workup

  1. customTo a 15 mL round-bottomed flask equipped
  2. stirringthe reaction mixture was stirred at ambient temp
  3. extractionextracted with EtOAc (3×15 mL)
  4. washwashed with sat'd NaHCO3 and brine
  5. dry with materialThe organic layers were then dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe sample was absorbed onto silica gel
  9. custompurified on a 40 g Isco Redi-sep® silica gel column that
  10. washThe product was eluted sample with CH2Cl2+2% (2M NH3 in MeOH)

Sources & evidence

ORD record
ord-340226b01309425e8a5f1586155368ba
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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