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Diisopropylethylamine → Ethyl 2-(5-bromo-3-(2,4-dimethoxybenzylamino)pyrazin-2-ylamino)acetate

HRID 1401172
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1401172
Br[C:2]1[C:3]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[CH3:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:19]=1[CH2:26][NH2:27].C(N(CC)C(C)C)(C)C>CS(C)=O>[Br:8][C:6]1[N:7]=[C:2]([NH:27][CH2:26][C:19]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:18]=2[O:17][CH3:16])[C:3]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:4][CH:5]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 5972502,4-DimethoxybenzylamineHCID 57550751Ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetate

Produkt 1

HCID 86696613Ethyl 2-(5-bromo-3-(2,4-dimethoxybenzylamino)pyrazin-2-ylamino)acetateAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl Sulfoxide
Lösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetate (See Example 1.C) (1.06 g, 3.13 mmol), (2,4-dimethoxyphenyl)methanamine (0.601 g, 3.60 mmol), N,N-diisopropylethylamine (1.63 mL, 9.38 mmol) and dimethylsulfoxide (1.6 mL) were combined in a microwave vial with a stirbar and heated in a microwave reactor at 150° C. for 2 h. The resulting mixture was purified using flash chromatography (5-60% ethyl acetate in hexane). Fractions containing the desired product were combined and concentrated nearly to dryness under reduced pressure. Ethyl acetate (2 mL) and hexane (18 mL) was added. The resulting solids were collected by vacuum filtration, washed with hexane and dried under high vacuum to give the desired product (0.636 g, 1.495 mmol, 48% yield) as a light pink solid. 1H NMR (300 MHz, DMSO-d6) δ (ppm) 7.24 (s, 1H), 7.19 (d, J=8.52 Hz, 1H), 7.11 (t, J=5.63 Hz, 1H), 6.84 (t, J=4.81 Hz, 1H), 6.59 (d, J=2.47 Hz, 1H), 6.50 (dd, J=2.20, 8.24 Hz, 1H), 4.37 (d, J=4.67 Hz, 2H), 3.96-4.15 (m, 4H), 3.81 (s, 3H), 3.75 (s, 3H), 1.17 (t, 3H); MS (ESI) m/z 425.3 [M]+, 426.9 [M+2]+.

Aufarbeitung

  1. customThe resulting mixture was purified
  2. additionFractions containing the desired product
  3. concentrationconcentrated nearly to dryness under reduced pressure
  4. additionEthyl acetate (2 mL) and hexane (18 mL) was added
  5. filtrationThe resulting solids were collected by vacuum filtration
  6. washwashed with hexane
  7. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-376f63ca93af437e872bc050873151dd
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08907087B2

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