Diisopropylethylamine → 4-Chloro-1-({5-[3-methyl-5-(trifluoromethyl)-4-isoxazolyl]-1,2,4-oxadiazol-3-yl}methyl)-2-propyl-1H-indole-5-carbonitrile

HRID 1188550

Reaktionsgleichung

Reaktionsgleichung von HRID 1188550
[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH2:19][CH2:20][CH3:21])[N:6]2[CH2:13]/[C:14](=[N:17]/[H])/[NH:15][OH:16].[CH3:22][C:23]1[C:27]([C:28](O)=O)=[C:26]([C:31]([F:34])([F:33])[F:32])[O:25][N:24]=1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH2:19][CH2:20][CH3:21])[N:6]2[CH2:13][C:14]1[N:17]=[C:28]([C:27]2[C:23]([CH3:22])=[N:24][O:25][C:26]=2[C:31]([F:34])([F:32])[F:33])[O:16][N:15]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27756453-Methyl-5-(trifluoromethyl)-1,2-oxazole-4-carboxylic acidHCID 178506478HCID 178506478, Verbindung

Produkt 1

HCID 578004054-Chloro-1-({5-[3-methyl-5-(trifluoromethyl)-4-isoxazolyl]-1,2,4-oxadiazol-3-yl}methyl)-2-propyl-1H-indole-5-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Synthesized as described in Example 32A and Example 33 using (1Z)-2-(4-chloro-5-cyano-2-propyl-1H-indol-1-yl)-N-hydroxyethanimidamide (0.030 g, 0.1 mmol) in anhydrous THF (5 mL) with propanephosphonic acid cyclic anhydride (T3P) (0.034 g, 0.12 mmol), 3-methyl-5-(trifluoromethyl)-4-isoxazolecarboxylic acid (0.0195 g, 0.1 mmol) and DIEA (0.016 mg, 0.12 mmol) and stirred at rt for 1 h and then heated at 120° C. for 2 h in the microwave: 1H NMR (400 MHz, CDCl3-d) δ 7.89 (s, 1H), 7.52 (d, J=8.4 Hz, 1H), 7.46 (d, J=8.4 Hz, 1H), 5.47 (s, 2H), 2.97 (t, 2H), 2.55 (s, 3H), 1.79-1.70 (m, 2H), 1.05 (t, 3H); MS (ES) m/z 450 (M+1).

Aufarbeitung

  1. customSynthesized
  2. temperatureheated at 120° C. for 2 h in the microwave

Quellen und Nachweise

ORD-Eintrag
ord-659e7d609fee47c5bc2b54bfcc932376
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673948B2

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