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PyBOP → HCID 178489409, Verbindung

HRID 2388967
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2388967
[NH2:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([C:12]2[CH:13]=[C:14]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH3:28])=[N:19][NH:18][C:15]3=[N:16][CH:17]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.[CH3:62][N:63]([CH3:69])[CH:64]1[CH2:68][CH2:67][NH:66][CH2:65]1>CN(C=O)C.C(#N)C>[NH2:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([C:12]2[CH:13]=[C:14]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH3:28])=[N:19][NH:18][C:15]3=[N:16][CH:17]=2)=[CH:7][C:3]=1[C:4]([N:66]1[CH2:67][CH2:68][CH:64]([N:63]([CH3:69])[CH3:62])[CH2:65]1)=[O:6]
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Komponenten

6

Edukt 3

HCID 2724699PyBOPHCID 27585193-(Dimethylamino)pyrrolidineHCID 178489410HCID 178489410, Verbindung

Produkt 1

HCID 178489409HCID 178489409, VerbindungAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

25 mg (66 μmol) of 2-amino-3-fluoro-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzoic acid and 72 mg (0.14 mmol) of (benzotriazol-1-yloxy)tripyrrolidino-phosphonium hexafluorophosphate were dissolved in a mixture of 200 μL of DMF and 1 mL of acetonitrile. 100 μL (approx. 0.88 mmol, density unknown) of 3-(dimethylamino)pyrrolidine was added and the resulting mixture was irradiated in a Personal Chemistry® Optimizer to 100° C. for 30 min. The resulting mixtures was evaporated and the residue purified by flash chromatography on amine functionalized silica gel (Teledyne ISCO Inc.) using a gradient of ethyl acetate containing 15% of methanol in hexanes. The resulting material was then purified by mass-triggered reverse-phase HPLC to afford 2.9 mg (6 μmol, 10%) of {2-amino-3-fluoro-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-(3-di-methylamino-pyrrolidin-1-yl)-methanone as a colorless solid. 1H NMR (500 MHz, DMSO-d6) δ 8.78 (d, 1H), 8.24 (s, br., 1H), 7.64 (dd, 1H), 7.55 (d(m), 1H), 7.46 (ddd, 1H), 7.38 (m, br., 1H), 7.21 (d, 1H), 7.09 (ddd, 1H), 5.45 (m, br., 2H), 3.83 (s, 3H), 3.75 (m, br. 1H), 3.64 (m, br. 1H), 3.47 (m, br. 1H), 3.24 (m, br. 1H), 2.18 (s, br. 3H), 2.09 (s, br. 3H), 2.01 (m, br. 1H), 1.80-1.65 (m, 2H), MS: m/z 475.2 (M+H+).

Aufarbeitung

  1. customthe resulting mixture was irradiated in a Personal Chemistry® Optimizer to 100° C. for 30 min
  2. customThe resulting mixtures was evaporated
  3. customthe residue purified by flash chromatography on amine functionalized silica gel (Teledyne ISCO Inc.)
  4. customThe resulting material was then purified by mass-triggered reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-25fa39594d374bcea931284dbf5f6226
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08268994B2

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