Phenylacetyl chloride → 5-(4-Acetoxyphenyl)-3-benzyl-2-(phenylacetylamino)pyrazine

HRID 1970790

Reaktionsgleichung

Reaktionsgleichung von HRID 1970790
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:14]([NH2:17])=[N:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:25]1([CH2:31][C:32](Cl)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:12]=[C:13]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:14]([NH:17][C:32](=[O:33])[CH2:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:15][CH:16]=2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 7679Phenylacetyl chlorideHCID 516892Sodium BicarbonateHCID 670035525-(4-Acetoxyphenyl)-2-amino-3-benzylpyrazine

Produkt 1

HCID 670032925-(4-Acetoxyphenyl)-3-benzyl-2-(phenylacetylamino)pyrazineAusbeute 20,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Under an argon atmosphere, 5-(4-acetoxyphenyl)-2-amino-3-benzylpyrazine (c-19) (194 mg, 607 μmol) was dissolved in pyridine (2 mL) and to this was added 4-(dimethylamino)pyridine (7.8 mg, 64 μmol) and cooled to 0° C. To this was added phenylacetyl chloride (160 μL, 1.21 mmol) and stirred for 2 h after warming to room temperature. To this was added saturated aqueous solution of sodium bicarbonate to stop the reaction and after collecting the precipitate by filtration using a Kiriyama funnel, the residue was dried in vacuo to give 5-(4-acetoxyphenyl)-3-benzyl-2-(phenylacetylamino)pyrazine (c-30) as a colorless solid (53.9 mg, 20.3%). Rf=0.24 (n-hexane/ethyl acetate=3/2). Mp. 228-231° C. UV (MeOH, 0.3% DMSO) λmax (log ε) 318 (4.19), 290 (4.17), 259 (4.24). 1H NMR (400 MHz, DMSO-d6) δ 2.29 (s, 3H), 3.68 (s, 2H), 4.07 (s, 2H), 7.01-7.08 (AA′BB′, 2H), 7.11-7.22 (m, 3H), 7.23-7.29 (m, 3H), 7.31-7.38 (m, 4H), 8.07-8.14 (AA′BB′, 2H), 8.93 (s, 1H), 10.57 (s, 1H). IR (KBr, cm−1) 706, 851, 918, 1157, 1206, 1223, 1346, 1366, 1410, 1449, 1495, 1543, 1576, 1670, 1755, 3248. HRMS (FAB+) m/z 438.1806 (M+H, C27H24N3O3 requires 438.1818).

Aufarbeitung

  1. temperatureafter warming to room temperature
  2. customthe reaction
  3. customafter collecting the precipitate
  4. filtrationby filtration
  5. customthe residue was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-efb103485de240f2a87b3205377bc529
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431525B2

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