Sodium hydride → HCID 86686949, Verbindung

HRID 2284919Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2284919
[NH2:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@H:5]([OH:12])[CH2:4][CH2:3]1.[H-].[Na+].F[C:16]1[CH:17]=[CH:18][C:19]2[N:20]([C:22]([CH2:25][CH2:26][N:27]3[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]3)=[N:23][N:24]=2)[CH:21]=1>CN(C=O)C>[CH3:33][N:30]1[CH2:29][CH2:28][N:27]([CH2:26][CH2:25][C:22]2[N:20]3[CH:21]=[C:16]([O:12][C@H:5]4[C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[C@@H:2]([NH2:1])[CH2:3][CH2:4]4)[CH:17]=[CH:18][C:19]3=[N:24][N:23]=2)[CH2:32][CH2:31]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 86686674(1R,4S)-4-Amino-1,2,3,4-tetrahydronaphthalen-1-olHCID 86686948HCID 86686948, Verbindung

Produkt 1

HCID 86686949HCID 86686949, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Intermediate A (180 mg, 1.11 mmol) was added to a suspension of sodium hydride (60% in mineral oil, 133 mg, 3.33 mmol) in DMF (5 mL). The reaction was stirred for 20 min, then Intermediate 2b (310 mg, 1.11 mmol) was added in DMF (5 mL) and the resulting mixture heated to 60° C. for 3 h. After cooling, the reaction was quenched by dropwise addition of MeOH. The solution was loaded onto an SCX-2 cartridge, which was washed with MeOH and product eluted with 2M NH3 in MeOH. The residue was purified by FCC, using 2-20% [2M NH3 in MeOH] in DCM, to give the title compound (200 mg, 0.47 mmol, 43%). LCMS (Method 4): Rt 0.28 min, m/z 407 [MH+].

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe reaction was quenched by dropwise addition of MeOH
  3. washwas washed with MeOH and product
  4. washeluted with 2M NH3 in MeOH
  5. customThe residue was purified by FCC

Quellen und Nachweise

ORD-Eintrag
ord-ea4a709732e147598afae4ccfa5a664b
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145413B2

Notizen zur Reaktion

Wird geladen…