Triethylamine → HCID 71509800, Verbindung

HRID 1499798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1499798
Cl.Cl.[NH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]2[N:10]([CH:16]([C:18]3[C:19]([O:31][CH3:32])=[C:20]([CH:27]4[CH2:30][NH:29][CH2:28]4)[C:21]([CH3:26])=[C:22]([CH:25]=3)[C:23]#[N:24])[CH3:17])[N:11]=[C:12]([CH:13]([F:15])[F:14])[C:5]=12.[Si]([O:50][C@@H:51]([CH3:54])[CH:52]=O)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl.O1CCCC1>[NH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]2[N:10]([CH:16]([C:18]3[C:19]([O:31][CH3:32])=[C:20]([CH:27]4[CH2:30][N:29]([CH2:52][C@@H:51]([OH:50])[CH3:54])[CH2:28]4)[C:21]([CH3:26])=[C:22]([CH:25]=3)[C:23]#[N:24])[CH3:17])[N:11]=[C:12]([CH:13]([F:14])[F:15])[C:5]=12

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 5049666Sodium triacetoxyborohydrideHCID 10828944(2S)-2-{[tert-Butyl(diphenyl)silyl]oxy}propanalHCID 86677719HCID 86677719, Verbindung

Produkt 1

HCID 71509800HCID 71509800, VerbindungAusbeute 6,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mixture of 5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-azetidin-3-yl-4-methoxy-2-methylbenzonitrile dihydrochloride (25 mg, 0.051 mmol), (2S)-2-{[tert-butyl(diphenyl)silyl]oxy}propanal (18 mg, 0.057 mmol) and triethylamine (22 μL, 0.15 mmol) in methylene chloride (0.3 mL) was added sodium triacetoxyborohydride resin (45 mg, 0.10 mmol). The mixture was stirred overnight then filtered and concentrated. To the residue was added tetrahydrofuran (1.0 mL) and 1.0 M tetra-n-butylammonium fluoride in THF (0.51 mL, 0.51 mmol). The resulting mixture was stirred overnight at room temp. The solvent was evaporated and the crude material was purified using RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give 1.6 mg (6.6%) of the desired product. The product was isolated as a single diastereomer. LCMS calculated for C23H28F2N7O2 (M+H)+: m/z=472.2; Found: 472.2.

Aufarbeitung

  1. filtrationthen filtered
  2. concentrationconcentrated
  3. stirringThe resulting mixture was stirred overnight at room temp
  4. customThe solvent was evaporated
  5. customthe crude material was purified
  6. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-aa5ce9ab64b34b57a7dcc62d90cb182d
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199982B2

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