Trifluoroacetic acid → HCID 178484181, Verbindung

HRID 1919170Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1919170
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([OH:31])([C:27]([F:30])([F:29])[F:28])=[O:26].[NH:32]1[CH2:36][CH2:35][CH2:34][C@H:33]1[C:37]1[NH:38][C:39]([C:42]2[S:43][C:44]([C:47]3[S:51][C:50]([C:52]4[NH:56][C:55]([C@@H:57]5[CH2:61][CH2:60][CH2:59][NH:58]5)=[N:54][CH:53]=4)=[N:49][CH:48]=3)=[CH:45][N:46]=2)=[CH:40][N:41]=1.Cl.[CH3:63][N:64]([CH3:75])[C@H:65]([C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)[C:66](O)=[O:67].C[CH2:77][N:78]([CH:82]([CH3:84])[CH3:83])[CH:79](C)C>CN(C)C=O.CO.O>[F:28][C:27]([F:30])([F:29])[C:25]([O-:31])=[O:26].[S:43]1[C:44]([C:47]2[S:51][C:50]([C:52]3[N:56]=[C:55]([C@@H:57]4[CH2:61][CH2:60][CH2:59][N:58]4[C:83](=[O:26])[C@@H:82]([C:84]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[N:78]([CH3:77])[CH3:79])[NH:54][CH:53]=3)=[N:49][CH:48]=2)=[CH:45][N:46]=[C:42]1[C:39]1[N:38]=[C:37]([C@@H:33]2[CH2:34][CH2:35][CH2:36][N:32]2[C:66](=[O:67])[C@@H:65]([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[N:64]([CH3:75])[CH3:63])[NH:41][CH:40]=1

Komponenten

10

Edukt 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45835119(R)-a-(Dimethylamino)benzeneacetic acid HClHCID 53233526HCID 53233526, Verbindung

Produkt 2

HCID 84468TrifluoroacetateHCID 178484181HCID 178484181, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

HATU (66 mg, 0.17 mmol) was added to a stirred solution of a TFA salt of 2,2′-bis(2-((2S)-2-pyrrolidinyl)-1H-imidazol-5-yl)-5,5′-bi-1,3-thiazole (40 mg, 0.045 mmol), (R)-2-(dimethylamino)-2-phenylacetic acid hydrochloride (39 mg, 0.18 mmol) and DIEA (0.078 mL, 0.45 mmol) in dimethylformamide (2 mL) at room temperature. The reaction was stirred for 3 h, diluted with methanol (2 mL) and water (2 mL) and stirred for 15 min. The reaction mixture was concentrated in vacuo to dryness and purified by preparative HPLC (Waters Sunfire C18 column 30×150 mm 5 u, eluted with a gradient of 10 to 80% acetonitrile/water/0.1% TFA). Fractions containing the desired product were concentrated to yield a trifluoroacetate salt of (1R,1′R)-2,2′-(5,5′-Bi-1,3-thiazole-2,2′-diylbis(1H-imidazole-4,2-diyl(2S)-2,1-pyrrolidinediyl))bis(N,N-dimethyl-2-oxo-1-phenylethanamine) (18 mg, 0.015 mmol, 34% yield) as an orange solid.

Aufarbeitung

  1. stirringstirred for 15 min
  2. concentrationThe reaction mixture was concentrated in vacuo to dryness
  3. custompurified by preparative HPLC (Waters Sunfire C18 column 30×150 mm 5 u
  4. washeluted with a gradient of 10 to 80% acetonitrile/water/0.1% TFA)
  5. additionFractions containing the desired product
  6. concentrationwere concentrated

Quellen und Nachweise

ORD-Eintrag
ord-0c5fe72377ee41a6a1b80e06c60bf77c
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618153B2

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