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Hydrochloric Acid → N-(2-((4-(2-Hydroxypropan-2-yl)thiazol-2-yl)methyl)-2H-1,2,3-triazol-4-yl)-2-methyl-5-(m-tolyl)oxazole-4-carboxamide

HRID 527234
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 527234
N#N.[C:3]([C:6]1[N:7]=[C:8]([CH2:11][N:12]2[N:16]=[C:15]([NH:17][C:18]([C:20]3[N:21]=[C:22]([CH3:32])[O:23][C:24]=3[C:25]3[CH:26]=[C:27]([CH3:31])[CH:28]=[CH:29][CH:30]=3)=[O:19])[CH:14]=[N:13]2)[S:9][CH:10]=1)(=[O:5])[CH3:4].[CH3:33][Al](C)C.[Cl-].[NH4+].Cl>C(Cl)Cl.CCCCCCC>[OH:5][C:3]([C:6]1[N:7]=[C:8]([CH2:11][N:12]2[N:16]=[C:15]([NH:17][C:18]([C:20]3[N:21]=[C:22]([CH3:32])[O:23][C:24]=3[C:25]3[CH:26]=[C:27]([CH3:31])[CH:28]=[CH:29][CH:30]=3)=[O:19])[CH:14]=[N:13]2)[S:9][CH:10]=1)([CH3:33])[CH3:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 42644151N-(2-((4-acetylthiazol-2-yl)methyl)-2H-1,2,3-triazol-4-yl)-2-methyl-5-(m-tolyl)oxazole-4-carboxamide

Produkt 1

HCID 67967927
N-(2-((4-(2-Hydroxypropan-2-yl)thiazol-2-yl)methyl)-2H-1,2,3-triazol-4-yl)-2-methyl-5-(m-tolyl)oxazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8900HeptaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of N-(2-((4-acetylthiazol-2-yl)methyl)-2H-1,2,3-triazol-4-yl)-2-methyl-5-(m-tolyl)oxazole-4-carboxamide (example 75 from WO 2009/077990; 50 mg, 0.12 mmol) in CH2Cl2 (1.1 mL) was treated at 0° C. with AlMe3 (0.3 mL of a 1.0M solution in heptane, 0.3 mmol) and the resulting mixture was stirred for 2 h at 0° C. The reaction mixture was carefully poured into a sat. aq. solution of ammonium chloride (5 mL) and diluted with CH2Cl2 (10 mL). 1N HCl (5 mL) was then added. The layers were separated and the org. phase was dried over Na2SO4, filtered and the solvents were removed under reduced pressure. Purification of the residue by FC (1:1 hept-EA) gave the title compound as a colorless oil: TLC: rf (1:1 hept-EA)=0.20. LC-MS-conditions 02: tR=0.88 min, [M+H]+=438.94.

Aufarbeitung

  1. customThe layers were separated
  2. dry with materialphase was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by FC (1:1 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-240e05d4750a48748730a2a6854a9157
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09346793B2

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