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Diisopropylethylamine → HCID 178509947, Verbindung

HRID 1874897
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1874897
[NH2:1][CH2:2][C:3]1[C:4]([F:21])=[C:5]([O:10][C:11]2[C:12]([Cl:20])=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1.[Cl:22][C:23]1[N:24]=[CH:25][N:26](COCC[Si](C)(C)C)[C:27]=1[C:28](O)=[O:29].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[Cl:22][C:23]1[N:24]=[CH:25][NH:26][C:27]=1[C:28]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([O:10][C:11]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:13]([C:14]#[N:15])[C:12]=2[Cl:20])[C:4]=1[F:21])=[O:29]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 684855334-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acidHCID 684876593-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-2,5-dichlorobenzonitrile

Produkt 1

HCID 178509947
HCID 178509947, Verbindung
Ausbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-2,5-dichlorobenzonitrile (0.062 g, 0.181 mmol), 4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid (0.05 g, 0.181 mmol) and DIPEA (0.063 mL, 0.361 mmol) were combined in THF (2 mL) and treated with HATU (0.076 g, 0.199 mmol) at 25° C. for 6 h with stirring. The reaction mixture was concentrated to dryness, dissolved in DCM, washed with saturated aqueous NaHCO3, dried over MgSO4, filtered and concentrated to dryness. The residue was dissolved in DCM (2.5 mL) and treated with TFA (2.5 mL) at 25° C. for 16 h. The reaction mixture was concentrated to dryness, dissolved in DCM, washed with saturated aqueous NaHCO3, dried over MgSO4, filtered and concentrated to dryness. The resultant solid was recrystallized from boiling EtOH, cooled in an ice bath and filtered to give 4-chloro-N-({4-chloro-3-[(2,5-dichloro-3-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1H-imidazole-5-carboxamide (0.067 g, 0.141 mmol, 78% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.18 (br. s., 1H), 8.27 (s, 1H), 8.02 (d, J=2.06 Hz, 1H), 7.78 (s, 1H), 7.53 (d, J=8.38 Hz, 1H), 7.40 (t, J=7.69 Hz, 1H), 7.25 (d, J=1.65 Hz, 1H), 4.53 (d, 2H). LC-MS (ES−) m/z 471.01, 473.00, 474.99 [M−1]. LC-MS (ES+) m/z 472.91, 474.92, 476.90 [M+H].

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to dryness
  2. dissolutiondissolved in DCM
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. dissolutionThe residue was dissolved in DCM (2.5 mL)
  8. additiontreated with TFA (2.5 mL) at 25° C. for 16 h
  9. concentrationThe reaction mixture was concentrated to dryness
  10. dissolutiondissolved in DCM
  11. washwashed with saturated aqueous NaHCO3
  12. dry with materialdried over MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated to dryness
  15. customThe resultant solid was recrystallized
  16. temperaturecooled in an ice bath
  17. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-8990912a160941688be5b7ea9bccea68
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08304419B2

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