1-Butanol → 6-(4-Hydroxyphenyl)-1-(piperidin-3-ylmethyl)-1H-imidazo[4,5-B]pyrazin-2(3H)-one

HRID 388141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 388141
[NH2:1][C:2]1[C:3]([NH:9][CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]2)=[N:4][C:5](Br)=[CH:6][N:7]=1.BrC1N=[C:27](N)[C:28](N)=NC=1.NCC1CCCN([C:41](OC(C)(C)C)=[O:42])C1.C(N(C(C)C)CC)(C)C.[CH2:57]([OH:61])[CH2:58][CH2:59][CH3:60]>>[OH:61][C:57]1[CH:28]=[CH:27][C:60]([C:5]2[N:4]=[C:3]3[N:9]([CH2:10][CH:11]4[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]4)[C:41](=[O:42])[NH:1][C:2]3=[N:7][CH:6]=2)=[CH:59][CH:58]=1

Komponenten

6

Edukt 5

HCID 2631-ButanolHCID 81531DiisopropylethylamineHCID 27564831-Boc-3-(aminomethyl)piperidineHCID 27718575-Bromopyrazine-2,3-diamineHCID 86626415tert-Butyl 3-((3-amino-6-bromopyrazin-2-ylamino)methyl)piperidine-1-carboxylate

Produkt 1

HCID 1358710236-(4-Hydroxyphenyl)-1-(piperidin-3-ylmethyl)-1H-imidazo[4,5-B]pyrazin-2(3H)-oneAusbeute 61 %

Versuchsvorschrift

tert-Butyl 3-((3-amino-6-bromopyrazin-2-ylamino)methyl)piperidine-1-carboxylate. In a sealed tube, a solution of 5-bromopyrazine-2,3-diamine (1.88 g, 7.46 mmol), tert-butyl 3-(aminomethyl)piperidinecarboxylate (2.0 g, 9.33 mmol), diisopropylethylamine (1.95 mL, 11.19 mmol) in n-butanol (200 mL) was heated at 120° C. for 17 h. The volatiles were removed under reduced pressure. The residue was taken up in hexanes and sonicated. The resulting precipitate was collected by filtration to provide the title compound (1.7 g, 61%). MS (ESI) m/z 387.3 [M+1]+.

Aufarbeitung

  1. customThe volatiles were removed under reduced pressure
  2. customsonicated
  3. filtrationThe resulting precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-52aa00ac4ee7497b874f39c5227c01b9
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372976B2

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