Water → 1-Hydroxybenzotriazole

HRID 2285096Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2285096
[OH2:1].F[C:3]1[CH:4]=[CH:5][C:6]([NH:9][NH2:10])=N[CH:8]=1.C(OC(C[CH2:19][N:20]1CCC[C@H]1C(O)=O)=O)(C)(C)C>CN(C=O)C.C(Cl)CCl>[CH:3]1[CH:4]=[CH:5][C:6]2[N:9]([OH:1])[N:10]=[N:20][C:19]=2[CH:8]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 199167865-Fluoro-2-hydrazinylpyridineHCID 89623862HCID 89623862, Verbindung

Produkt 1

HCID 757711-HydroxybenzotriazoleAusbeute 260,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

H2O (695 mg, 3.62 mmol) was added to a suspension of (5-fluoro-pyridin-2-yl)-hydrazine (418 mg, 3.29 mmol), Intermediate 84b (840 mg, 3.29 mmol), and EDC (44.0 mg, 0.33 mmol) in DMF (25.0 mL). The reaction was stirred overnight then partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-10% [2M NH3 in MeOH] in DCM, to give the title compound (1.16 g, 99%). LCMS (Method 1): Rt 2.06 mins, m/z 353.3 [MH+].

Aufarbeitung

  1. customthen partitioned between EtOAc and water
  2. extractionThe aqueous layer was then extracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by FCC

Quellen und Nachweise

ORD-Eintrag
ord-fa78d6eef1434a9d842907d962b23d25
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145413B2

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