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Triethylamine → HCID 68159047, Verbindung

HRID 514224
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 514224
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]4[CH2:23][CH:22]4[NH2:24])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.CCN(CC)CC.Cl[C:35]([O:37][C:38]1[C:43]([CH3:44])=[CH:42][C:41]([CH3:45])=[CH:40][C:39]=1[CH3:46])=[O:36]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:26][C:2]([F:1])([F:25])[O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]4[CH2:23][CH:22]4[NH:24][C:35](=[O:36])[O:37][C:38]4[C:43]([CH3:44])=[CH:42][C:41]([CH3:45])=[CH:40][C:39]=4[CH3:46])=[CH:17][CH:16]=3)=[N:11]2)=[CH:8][CH:9]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 11106338HCID 11106338, VerbindungHCID 68158720HCID 68158720, Verbindung

Produkt 1

HCID 68159047HCID 68159047, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

2-{4-[1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]phenyl}cyclopropylamine (46.0 mg, 0.13 mmol, 1.0 equiv) was dissolved in CH2Cl2 (0.55 mL) under N2. 4-Dimethylaminopyridine (DMAP; 0.8 mg, 0.006 mmol, 0.05 equiv) and Et3N (27 μL, 0.19 mmol, 1.5 equiv) were added, followed by mesityl chloroformate prepared above (33 mg, 0.17 mmol, 1.2 equiv). The reaction was stirred for 5 min and was then quenched with NaHCO3 (aq). The layers were separated, and the aqueous layer was extracted twice more with CH2Cl2. The combined organic extracts were concentrated, and the crude product was purified by silica gel chromatography (EtOAc-hexanes gradient) to afford the title compound as a white solid (53.0 mg, 79%): mp 199-202° C.; 1H NMR (400 MHz, CDCl3, data for major rotamer) δ 8.54 (s, 1H), 8.08 (d, J=8.3 Hz, 2H), 7.78 (d, J=9.0 Hz, 2H), 7.39 (d, J=0.7 Hz, 2H), 7.32-7.21 (m, 2H), 6.86 (s, 2H), 5.71-5.36 (m, 0.7H), 5.22-4.82 (m, 0.3H), 3.09-2.81 (m, 1H), 2.26 (s, 4H), 2.17 (s, 6H), 1.43-1.26 (m, 2H); ESIMS m/z 523 (M+H).

Aufarbeitung

  1. customprepared above (33 mg, 0.17 mmol, 1.2 equiv)
  2. customwas then quenched with NaHCO3 (aq)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted twice more with CH2Cl2
  5. concentrationThe combined organic extracts were concentrated
  6. customthe crude product was purified by silica gel chromatography (EtOAc-hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-29914bea9dc34b0ab36f5d2a99589c96
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09107410B2

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