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Diisopropylethylamine → HCID 178522956, Verbindung

HRID 1874915
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1874915
[Br:1][C:2]1[CH:3]=[C:4]([F:20])[C:5]([Cl:19])=[C:6]([O:8][C:9]2[C:10]([F:18])=[C:11]([CH2:16][NH2:17])[CH:12]=[CH:13][C:14]=2[Cl:15])[CH:7]=1.[Cl:21][C:22]1[N:23]=[CH:24][N:25](COCC[Si](C)(C)C)[C:26]=1[C:27](O)=[O:28].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>[Br:1][C:2]1[CH:3]=[C:4]([F:20])[C:5]([Cl:19])=[C:6]([O:8][C:9]2[C:10]([F:18])=[C:11]([CH2:16][NH:17][C:27]([C:26]3[NH:25][CH:24]=[N:23][C:22]=3[Cl:21])=[O:28])[CH:12]=[CH:13][C:14]=2[Cl:15])[CH:7]=1
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 68480394({3-[(5-Bromo-2-chloro-3-fluorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amineHCID 684855334-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid

Produkt 1

HCID 178522956
HCID 178522956, Verbindung
Ausbeute 51,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

({3-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amine (0.069 g, 0.181 mmol), 4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid (0.050 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. overnight with stirring. The reaction mixture was concentrated to dryness, dissolved in DCM, washed with water, 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 3 days. 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 EtOH, cooled in an ice bath and filtered to give N-({3-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1H-imidazole-5-carboxamide (0.048 g, 0.094 mmol, 51.9% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.17 (br. s., 1H), 8.27 (br. s., 1H), 7.78 (s, 1H), 7.63 (dd, J=8.52, 1.79 Hz, 1H), 7.53 (d, J=8.52 Hz, 1H), 7.39 (m, 1H), 6.76 (s, 1H), 4.54 (d, 2H). LC-MS (ES−) m/z 507.94, 509.95, 511.94 [M−1]. LC-MS (ES+) m/z 509.88, 511.87, 513.88 [M+H].

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to dryness
  2. dissolutiondissolved in DCM
  3. washwashed with water
  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 3 days
  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 from EtOH
  16. temperaturecooled in an ice bath
  17. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-5d7451a8528447ab905ec8f6b14d7f98
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08304419B2

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