Diisopropylethylamine → HCID 46851711, Verbindung

HRID 1262203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1262203
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:14]=3)[N:6]2[N:5]=1)=O.[O:23]=[S:24]1(=[O:38])[CH2:29][CH2:28][N:27]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)[CH2:26][CH2:25]1.C(N(CC)C(C)C)(C)C>COCC(O)C>[O:38]=[S:24]1(=[O:23])[CH2:25][CH2:26][N:27]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([NH:37][C:4]3[N:9]=[CH:8][C:7]4=[CH:10][CH:11]=[C:12]([C:13]5[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH3:22])(=[O:20])=[O:21])[CH:14]=5)[N:6]4[N:5]=3)=[CH:33][CH:32]=2)[CH2:28][CH2:29]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27796824-(4-Aminobenzyl)thiomorpholine 1,1-dioxideHCID 66711400HCID 66711400, Verbindung

Produkt 1

HCID 46851711HCID 46851711, VerbindungAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 79001-Methoxy-2-propanolLösungsmittel

Versuchsvorschrift

2-Methanesulfinyl-7-(3-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (100 mg, 0.298 mmol), 4-(1,1-dioxo-1$1(6)-thiomorpholin-4-ylmethyl)-phenylamine (158 mg, 0.656 mmol), and N,N-diisopropylethylamine (114 μL, 0.656 mmol) were placed in 1-methoxy-2-propanol (728 μL). The reaction was microwaved on 300 watts, 170° C. for 8 hours. Purification by prep-HPLC using a gradient of 10-70% AcN/water both containing 0.1% TFA as the eluting solvent. The product was then free based to obtain the title compound as an orange foam (18 mg, 12%). LCMS (m/e) 512 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.76 (s, 1H), 8.71 (s, 1H), 8.34 (d, 1H, J=7.9 Hz), 7.94 (d, 1H, J=7.8 Hz), 7.73-7.66 (m, 1H), 7.58 (d, 2H, J=8.3 Hz), 7.31 (d, 2H, J=8.3 Hz), 7.05 (d, 1H, J=4.8 Hz), 6.99 (s, 1H), 6.87 (d, 1H, J=4.8 Hz), 3.63 (s, 2H), 3.09 (s, 3H), 3.09-3.03 (m, 4H), 3.03-2.94 (m, 4H).

Aufarbeitung

  1. customThe reaction was microwaved on 300 watts, 170° C. for 8 hours
  2. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-99898eff6bdf45e39fd7d43bbe25cca3
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471005B2

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