Diisopropylethylamine → HCID 58324460, Verbindung

HRID 1644986

Reaktionsgleichung

Reaktionsgleichung von HRID 1644986
O[CH2:2][C:3]1[CH:12]=[N:11][C:10]2[N:9]3[CH2:13][CH2:14][C@H:8]3[C:7](=[O:15])[NH:6][C:5]=2[CH:4]=1.[N:16]1([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[I-].C(C[P+](C)(C)C)#N.C(N(CC)C(C)C)(C)C>C(#N)CC.CO>[O:15]=[C:7]1[NH:6][C:5]2[CH:4]=[C:3]([CH2:2][N:19]3[CH2:18][CH2:17][N:16]([C:22]4[CH:23]=[CH:24][C:25]([C:26]#[N:27])=[CH:28][CH:29]=4)[CH2:21][CH2:20]3)[CH:12]=[N:11][C:10]=2[N:9]2[CH2:13][CH2:14][C@@H:8]12

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 27339954-(Piperazin-1-yl)benzonitrileHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 58324372(S)-3-(hydroxymethyl)-7,8-dihydro-5H-azeto[1,2-a]pyrido[3,2-e]pyrazin-6(6aH)-one

Produkt 1

HCID 58324460HCID 58324460, VerbindungAusbeute 6,25 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 7854PropionitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

(S)-3-(hydroxymethyl)-7,8-dihydro-5H-azeto[1,2-a]pyrido[3,2-e]pyrazin-6(6aH)-one (103 mg, 0.5 mmol), 4-(piperazin-1-yl)benzonitrile (108 mg, 0.575 mmol), (cyanomethyl)trimethylphosphonium iodide (207 mg, 0.850 mmol) and N,N-diisopropylethylamine (0.437 ml, 2.500 mmol) were suspended in Propiononitrile (Volume: 1.502 ml) and heated in a closed vial at 90° C. for 23 h. The reaction mixture was cooled, diluted with MeOH (2 mL) and purified using preparative HPLC (basic phase). The fractions containing product were concentrated in vacuo and crystallized from water-methanol (3 mL, ˜5:1) The precipitate was filtered and dried in vacuum to afford (S)-4-(4-((6-oxo-6,6a,7,8-tetrahydro-5H-azeto[1,2-a]pyrido[3,2-e]pyrazin-3-yl)methyl)piperazin-1-yl)benzonitrile (11.7 mg, 0.031 mmol, 6.25% yield) as a light brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.37-2.47 (m, 4H) 2.68-2.80 (m, 1H) 2.94 (tt, J=10.67, 7.26 Hz, 1H) 3.30 (d, J=4.80 Hz, 4H) 3.36 (s, 2H) 3.87-4.00 (m, 1H) 4.21 (q, J=7.66 Hz, 1H) 4.93 (t, 1H) 6.98 (d, J=1.77 Hz, 1H) 7.00 (d, J=9.09 Hz, 2H) 7.57 (d, J=9.09 Hz, 2H) 7.65 (d, J=1.77 Hz, 1H) 10.34 (s, 1H). [M+H] calc'd for C21H22N6O, 374. found, 374.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. custompurified
  3. additionThe fractions containing product
  4. concentrationwere concentrated in vacuo
  5. customcrystallized from water-methanol (3 mL, ˜5:1) The precipitate
  6. filtrationwas filtered
  7. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-85ab62e1f00944bdb198b43c01befee9
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124606B2

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