Trifluoroacetic acid → HCID 89465782, Verbindung

HRID 334437

Reaktionsgleichung

Reaktionsgleichung von HRID 334437
FC(F)(F)C(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:22][C:23]1[CH:24]=[C:25]([S:30][C:31]2[CH:32]=[C:33]3[C:39]([NH2:40])=[N:38][NH:37][C:34]3=[N:35][CH:36]=2)[CH:26]=[C:27]([F:29])[CH:28]=1.[CH3:41][N:42]1[CH2:47][CH2:46][N:45]([C:48]2[CH:55]=[CH:54][C:51]([CH:52]=O)=[CH:50][CH:49]=2)[CH2:44][CH2:43]1>O1CCCC1.ClCCl>[F:22][C:23]1[CH:24]=[C:25]([S:30][C:31]2[CH:32]=[C:33]3[C:39]([NH:40][CH2:52][C:51]4[CH:50]=[CH:49][C:48]([N:45]5[CH2:44][CH2:43][N:42]([CH3:41])[CH2:47][CH2:46]5)=[CH:55][CH:54]=4)=[N:38][NH:37][C:34]3=[N:35][CH:36]=2)[CH:26]=[C:27]([F:29])[CH:28]=1

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acid2×HCID 7365334-(4-Methylpiperazin-1-yl)benzaldehydeHCID 5049666Sodium triacetoxyborohydride2×HCID 178509236HCID 178509236, Verbindung

Produkt 1

HCID 89465782HCID 89465782, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

41.5 μl of trifluoroacetic acid (0.539 mmol) and, in small fractions, 129 mg (0.611 mmol) of sodium triacetoxyborohydride are added to a solution of 100 mg (0.35 mmol) of 5-(3,5-difluorophenylthio)-1H-pyrazolo[3,4-b]pyridin-3-amine and 81 mg (0.395 mmol) of 4-(4-methylpiperazin-1-yl)benzaldehyde in 20 ml of a 1:1 mixture of dichloromethane and tetrahydrofuran. The reaction medium is stirred for 16 hours at room temperature. An additional fraction of 125 μl of trifluoroacetic acid and 388 mg of sodium triacetoxyborohydride are added and the reaction medium is stirred for an additional 24 hours. The solvent is then concentrated and the reaction medium extracted with ethyl acetate and washed using saturated sodium bicarbonate solution. The organic phases are combined, dried on magnesium sulfate and then concentrated to yield a yellow oil. A trituration of this oil in methanol leads to the isolation of 135 mg of a yellow solid.

Aufarbeitung

  1. stirringthe reaction medium is stirred for an additional 24 hours
  2. concentrationThe solvent is then concentrated
  3. extractionthe reaction medium extracted with ethyl acetate
  4. washwashed
  5. customdried on magnesium sulfate
  6. concentrationconcentrated
  7. customto yield a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-989af7569fa646248dd773bdda084e66
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883821B2

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