Trifluoroacetic acid → (4-(3-(azetidin-3-yl)pyrazin-2-yloxy)phenyl)(1H-benzo[d]imidazol-2-yl)methanone

HRID 2192021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192021
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:35]=[CH:34][C:15]([O:16][C:17]2[C:18]([CH:23]3[CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24]3)=[N:19][CH:20]=[CH:21][N:22]=2)=[CH:14][CH:13]=1)=[O:11].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:25]1[CH2:26][CH:23]([C:18]2[C:17]([O:16][C:15]3[CH:34]=[CH:35][C:12]([C:10]([C:2]4[NH:1][C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=5[N:3]=4)=[O:11])=[CH:13][CH:14]=3)=[N:22][CH:21]=[CH:20][N:19]=2)[CH2:24]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 59327110tert-butyl 3-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)azetidine-1-carboxylate

Produkt 1

HCID 59351448(4-(3-(azetidin-3-yl)pyrazin-2-yloxy)phenyl)(1H-benzo[d]imidazol-2-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 3-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)azetidine-1-carboxylate (175 mg, 0.371 mmol) in CH2Cl2 (1 mL) is added 2,2,2-trifluoroacetic acid (1.0 mL). The reaction was stirred at rt 1 h. The solution was concentrated and CH2Cl2 (5 mL) and saturated NaHCO3 (0.5 mL) was added. MgSO4 was added to remove water and the solution filtered and concentrated to give the crude amine as a dark green oil which was carried on to the next step without purification. (Note: An insoluble solid crashed out during the extraction, which later was identified as the desired crude amine product, which is sparingly soluble in CH2Cl2, but soluble in THF. The insoluble solid from the extraction was dissolved in THF, dried (MgSO4), concentrated, and combined with the material from aqueous extraction and carried on into the next step.

Aufarbeitung

  1. concentrationThe solution was concentrated
  2. additionCH2Cl2 (5 mL) and saturated NaHCO3 (0.5 mL) was added
  3. additionMgSO4 was added
  4. customto remove water
  5. filtrationthe solution filtered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-68d80052b93846e6af382ecc29f20425
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329700B2

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