Diisopropylethylamine → HCID 59170244, Verbindung

HRID 1446299

Reaktionsgleichung

Reaktionsgleichung von HRID 1446299
[CH3:1][C:2]1[C:6]([C:7]([OH:9])=O)=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:4][N:3]=1.[NH:16]1[CH2:20][CH2:19][CH2:18][CH:17]1[CH2:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH3:1][C:2]1[C:6]([C:7]([N:16]2[CH2:20][CH2:19][CH2:18][CH:17]2[CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[O:9])=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:4][N:3]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27765143-Methyl-5-phenylisoxazole-4-carboxylic acidHCID 32638763-(2-Pyrrolidinylmethyl)pyridine

Produkt 1

HCID 59170244HCID 59170244, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-Methyl-5-phenyl-4-isoxazolecarboxylic acid (40 mg, 0.197 mmol), 3-(pyrrolidin-2-ylmethyl)pyridine (50.5 mg, 0.215 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (86.2 mg, 0.268 mmol) and diisopropylethylamine (25.4 mg, 0.197 mmol) were mixed in dimethylformamide (1.0 mL) and stirred at room temperature. Solvent was evaporated in vacuo, and the residue was taken up in methanol (1 mL), filtered and purified by preparative chromatography. The combined fractions were partitioned between NaHCO3 (sat) and ethylacetate. The organic layer was washed with water and concentrated in vacuo to afford the title compound. HRMS (ESI, pos. ion) m/z calcd for C21H21N3O2: 347.1634, found 347.1642.

Aufarbeitung

  1. customSolvent was evaporated in vacuo
  2. filtrationfiltered
  3. custompurified by preparative chromatography
  4. customThe combined fractions were partitioned between NaHCO3 (sat) and ethylacetate
  5. washThe organic layer was washed with water
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-95b6aeec88fd4f12ad0a50e3f22fc281
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666888B2

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