Sodium hydride → HCID 86687165, Verbindung

HRID 2282620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2282620
[H-].[Na+].[NH2:3][C@@H:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C@H:7]([OH:14])[CH2:6][CH2:5]1.F[C:16]1[CH:17]=[CH:18][C:19]2[N:20]([C:22]([N:25]([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])=[N:23][N:24]=2)[CH:21]=1>CN(C=O)C>[NH2:3][C@@H:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C@H:7]([O:14][C:16]2[CH:17]=[CH:18][C:19]3[N:20]([C:22]([N:25]([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:27])[CH3:28])=[N:23][N:24]=3)[CH:21]=2)[CH2:6][CH2:5]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 86686674(1R,4S)-4-Amino-1,2,3,4-tetrahydronaphthalen-1-olHCID 86687166HCID 86687166, Verbindung

Produkt 1

HCID 86687165HCID 86687165, VerbindungAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a suspension of sodium hydride (60% in mineral oil, 136 mg, 3.39 mmol) in DMF (5 mL) was added Intermediate A (138 mg, 0.85 mmol) and the reaction mixture was stirred for 15 min at RT. A solution of Intermediate 103b (200 mg, 0.85 mmol) in DMF (3 mL) was added and the reaction mixture was heated at 60° C. for 1 h. The reaction mixture was quenched by careful addition of MeOH and then loaded onto an SCX cartridge. The cartridge was washed with MeOH and the product eluted with 2M NH3 in MeOH. The product containing fractions were concentrated in vacuo and the resultant residue was purified by FCC on silica, using a gradient of 0-10% [2M NH3 in MeOH] in DCM, to give the title compound (220 mg, 68%). LCMS (Method 4): Rt 2.07 min, m/z 380 [MH+].

Aufarbeitung

  1. temperaturethe reaction mixture was heated at 60° C. for 1 h
  2. customThe reaction mixture was quenched by careful addition of MeOH
  3. washThe cartridge was washed with MeOH
  4. washthe product eluted with 2M NH3 in MeOH
  5. additionThe product containing fractions
  6. concentrationwere concentrated in vacuo
  7. customthe resultant residue was purified by FCC on silica

Quellen und Nachweise

ORD-Eintrag
ord-6eef2e58c180471396b5b1f09fc78e02
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139584B2

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