Triethylamine → HCID 21867318, Verbindung

HRID 630738

Reaktionsgleichung

Reaktionsgleichung von HRID 630738
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]2[C:15]([NH2:16])=[CH:14][C:13]([C:17]([CH3:20])([CH3:19])[CH3:18])=[N:12]2)[CH:6]=1)C.CCN(CC)CC.[BH4-].[Na+]>CCO.O>[NH2:16][C:15]1[N:11]([C:7]2[CH:6]=[C:5]([CH2:4][OH:3])[CH:10]=[CH:9][CH:8]=2)[N:12]=[C:13]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:14]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 4311764Sodium borohydride3×HCID 21867322ethyl 3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoate

Produkt 1

HCID 21867318HCID 21867318, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of Intermediate 29a (1.00 g, 3.48 mmol) and Et3N (265 μL, 1.91 mmol) in EtOH (35 mL) was added NaBH4 (198 mg, 5.23 mmol) and the suspension stirred at RT for 1.5 h. NaBH4 (198 mg, 5.23 mmol) was added and the suspension stirred for a further 19 h. NaBH4 (1.31 g, 34.8 mmol) was added and the suspension stirred for a further 24 h, then diluted with water and extracted with DCM. The combined organics were dried and concentrated in vacuo. The residue was purified by FCC, using 0-10% [2M NH3 in MeOH] in DCM, to give the title compound as a white solid (740 mg, 87%). LCMS (Method 3): Rt 2.05 min, m/z 246 [MH+].

Aufarbeitung

  1. stirringthe suspension stirred for a further 19 h
  2. stirringthe suspension stirred for a further 24 h
  3. extractionextracted with DCM
  4. customThe combined organics were dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by FCC

Quellen und Nachweise

ORD-Eintrag
ord-43a0898a00d6435a80328f902108cfce
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315503B2

Verknüpfte Notizen

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