Trifluoroacetic acid → (S)-N-(2,2-dimethyl-1-(3-methyl-1,2,4-oxadiazol-5-yl)propyl)-3-phenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxamide

HRID 1971098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1971098
[CH3:1][C:2]([CH3:36])([CH3:35])[C@H:3]([NH:10][C:11]([C:13]1[N:14]=[C:15]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:16]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][C:17]=12)=[O:12])[C:4]1[O:8][N:7]=[C:6]([CH3:9])[N:5]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]([CH3:36])([CH3:35])[C@H:3]([NH:10][C:11]([C:13]1[N:14]=[C:15]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:16]2[CH2:21][CH2:20][NH:19][CH2:18][C:17]=12)=[O:12])[C:4]1[O:8][N:7]=[C:6]([CH3:9])[N:5]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 57635507(S)-tert-butyl 1-(2,2-dimethyl-1-(3-methyl-1,2,4-oxadiazol-5-yl)propylcarbamoyl)-3-phenyl-5,6-dihydroimidazo[1,5-a]pyrazine-7(8H)-carboxylate

Produkt 1

HCID 57635129(S)-N-(2,2-dimethyl-1-(3-methyl-1,2,4-oxadiazol-5-yl)propyl)-3-phenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxamideAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Intermediate 22D (170 mg, 0.34 mmol) was dissolved in DCM (2 mL) and TFA (0.5 mL) was added. The resulting mixture was stirred for 2 h. The mixture was concentrated, neutralized with NaHCO3 saturated solution and extracted several times with EtOAc. The combined organic extracts were washed successively with water and brine, dried over anhydrous Na2SO4, filtered and concentrated to give of Compound 282 (125 mg, 87%). 1H-NMR (400 MHz, CDCl3-d) δ: 1.09 (s, 9H), 2.40 (s, 3H), 3.78 (m, 2H), 4.11 (m, 2H), 5.01 (m, 2H), 5.37 (d, 1H), 7.35 (m, 3H), 7.64 (m, 2H), 7.78 (d, 1H), LCMS (+ESI) m/z 395.0 [M+H]+.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. extractionextracted several times with EtOAc
  3. washThe combined organic extracts were washed successively with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2df2187f88534a7bbd6524593731b256
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431565B2

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