Dimethylformamide → 1-(4-(7-(3-Cyanopyrazin-2-yl)-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea

HRID 1698002

Reaktionsgleichung

Reaktionsgleichung von HRID 1698002
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:16]3[CH2:22][CH2:21][NH:20][CH2:19][C:17]=3[N:18]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].Cl[C:30]1[C:31]([C:36]#[N:37])=[N:32][CH:33]=[CH:34][N:35]=1.CN(C)C=O.C(N(CC)C(C)C)(C)C>>[C:36]([C:31]1[C:30]([N:20]2[CH2:21][CH2:22][C:16]3[C:15]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)=[N:14][C:13]([C:10]4[CH:9]=[CH:8][C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[CH:12][CH:11]=4)=[N:18][C:17]=3[CH2:19]2)=[N:35][CH:34]=[CH:33][N:32]=1)#[N:37]

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2924653-Chloropyrazine-2-carbonitrileHCID 469130711-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl) phenyl)urea

Produkt 1

HCID 592393961-(4-(7-(3-Cyanopyrazin-2-yl)-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea

Versuchsvorschrift

1-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0506 g, 0.132 mmol) and 3-chloropyrazine-2-carbonitrile (0.0338 g, 0.242 mmol) were combined then added dry N,N-Dimethylformamide (0.910 mL, 11.8 mmol) followed by N,N-Diisopropylethylamine (0.0456 mL, 0.262 mmol). The reaction was microwaved on 200 watts, 120° C. for 30 minutes on a CEM microwave. The reaction mixture was purified by HPLC. 1H NMR (500 MHz, DMSO) δ 8.80 (s, 1H), 8.50 (d, J=2.2, 1H), 8.21 (d, J=8.7, 2H), 8.15 (d, J=2.2, 1H), 7.50 (d, J=8.7, 2H), 6.30 (t, J=5.5, 1H), 4.86 (s, 2 H), 4.00 (s, 2H), 3.74 (d, J=4.3, 4H), 3.49 (d, J=4.2, 4H), 3.12 (dt, J=13.8, 7.1, 3H), 2.85 (s, 2H), 1.06 (t, J=7.2, 3H). LC/MS-m/z+486.2 (M+H)+.

Aufarbeitung

  1. customThe reaction was microwaved on 200 watts, 120° C. for 30 minutes on a CEM microwave
  2. customThe reaction mixture was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-bb9992ebffe9457e8fdb32261df682c3
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163763B2

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