Hy-drazinium monoformate → (R)-N-(2-(1H-1,2,3-Triazol-1-yl)ethyl)-4-(7-(5-(1-aminoethyl)-2-fluoropyridin-4-yl)benzo[b]thiophen-2-yl)pyrimidin-2-amine

HRID 1640936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1640936
NN.C(O)=O.[N:6]1([CH2:11][CH2:12][NH:13][C:14]2[N:19]=[C:18]([C:20]3[S:24][C:23]4[C:25]([C:29]5[C:34]([C@H:35]([N:37]=[N+]=[N-])[CH3:36])=[CH:33][N:32]=[C:31]([F:40])[CH:30]=5)=[CH:26][CH:27]=[CH:28][C:22]=4[CH:21]=3)[CH:17]=[CH:16][N:15]=2)[CH:10]=[CH:9][N:8]=[N:7]1>C(O)C.[Ni]>[N:6]1([CH2:11][CH2:12][NH:13][C:14]2[N:19]=[C:18]([C:20]3[S:24][C:23]4[C:25]([C:29]5[C:34]([C@H:35]([NH2:37])[CH3:36])=[CH:33][N:32]=[C:31]([F:40])[CH:30]=5)=[CH:26][CH:27]=[CH:28][C:22]=4[CH:21]=3)[CH:17]=[CH:16][N:15]=2)[CH:10]=[CH:9][N:8]=[N:7]1

Komponenten

5

Edukt 2

HCID 46899473Hy-drazinium monoformateHCID 86641882(R)-N-(2-(1H-1,2,3-triazol-1-yl)ethyl)-4-(7-(5-(1-azidoethyl)-2-fluoropyridin-4-yl)benzo[b]thiophen-2-yl)pyrimidin-2-amine

Produkt 1

HCID 59332526(R)-N-(2-(1H-1,2,3-Triazol-1-yl)ethyl)-4-(7-(5-(1-aminoethyl)-2-fluoropyridin-4-yl)benzo[b]thiophen-2-yl)pyrimidin-2-amineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Add NH2NH2—HCOOH (Pre-prepared, 1 mL) to a solution of (R)—N-(2-(1H-1,2,3-triazol-1-yl)ethyl)-4-(7-(5-(1-azidoethyl)-2-fluoropyridin-4-yl)benzo[b]thiophen-2-yl)pyrimidin-2-amine (250 mg, 513.84 μmol) in ethanol (10 mL). Cool the mixture to 0° C. and add Raney Nickel (0.5 g, 8.52 mmol, wet with water as it packed). Stir the solution at RT for another 1.5 h, filter Raney Nickel out, and wash with methanol. Dilute filtrate with chloroform/IPA (3/1) and wash with saturated sodium carbonate. Dry the organic phase over sodium sulfate and concentrate in vacuo to give a brown tar. Purify the solid by passing through a FCC (10% methanol in DCM) to give the title compound as a pale brown solid (200 mg, 85%). MS (ES) m/z 461 [M+1]+.

Aufarbeitung

  1. filtrationfilter Raney Nickel out
  2. washwash with methanol
  3. washDilute filtrate with chloroform/IPA (3/1) and wash with saturated sodium carbonate
  4. dry with materialDry the organic phase over sodium sulfate
  5. concentrationconcentrate in vacuo
  6. customto give a brown tar
  7. customPurify the solid

Quellen und Nachweise

ORD-Eintrag
ord-ad8a51b426324816b9005d1675942a88
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08114872B2

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