Triphenylphosphine dibromide → 5-Bromo-3-(5-(thiophen-2-yl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

HRID 78615

Reaktionsgleichung

Reaktionsgleichung von HRID 78615
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]([NH:19][NH2:20])=O.BrP(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCN(C(C)C)C(C)C>C(#N)C>[Br:8][C:5]1[N:4]=[C:3]([C:9]2[O:11][C:17]([C:13]3[S:12][CH:16]=[CH:15][CH:14]=3)=[N:19][N:20]=2)[C:2]([NH2:1])=[N:7][CH:6]=1

Komponenten

6

Edukt 4

HCID 70579Triphenylphosphine dibromideHCID 73098Thiophene-2-carbohydrazideHCID 81531Diisopropylethylamine3×HCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

Produkt 1

HCID 594719085-Bromo-3-(5-(thiophen-2-yl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amineAusbeute 58,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

3-amino-6-bromo-pyrazine-2-carboxylic acid (3.2 g, 14.68 mmol) and thiophene-2-carbohydrazide (2.152 g, 14.68 mmol) were suspended in acetonitrile (48.00 mL) at room temperature and dibromo(triphenyl)phosphorane (24.79 g, 58.72 mmol) was added, followed byadditional acetonitrile (16.00 mL). The reaction mixture turned bright yellow in colour and was stirred at room temperature for 1 h. After this time, the reaction mixture cooled in an icebath and DIPEA (7.209 g, 9.716 mL, 55.78 mmol) was added dropwise. The reaction mixture was stirred in the ice bath for 1 h and then additional DIPEA (2.277 g, 3.069 mL, 17.62 mmol) added and the reaction mixture stirred for left for 30 mins and further DIPEA (1.897 g, 2.557 mL, 14.68 mmol) added. The reaction mixture was stirred for 1 h and then filtered. The solid was washed with ether, isolated and then triturated with acetonitrile and washed with ether to give the product as a yellow solid (2.776 g, 57% yield); 1H NMR (400.0 MHz, DMSO) 7.35 (s, 1H), 7.80 (br s, 2H), 7.98 (m, 1H), 8.04 (m, 1H) and 8.45 (s, 1H); MS (ES+) 326.04

Aufarbeitung

  1. additionwas added dropwise
  2. stirringthe reaction mixture stirred
  3. waitfor left for 30 mins
  4. stirringThe reaction mixture was stirred for 1 h
  5. filtrationfiltered
  6. washThe solid was washed with ether
  7. customisolated
  8. customtriturated with acetonitrile
  9. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-539a504bdf254e19943bf081b9102183
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841308B2

Verknüpfte Notizen

Wird geladen…