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Sodium Carbonate → (4-(5-Amino-6-(5-phenyl-1,3,4-thiadiazol-2-yl)pyrazin-2-yl)phenyl)(1,4-diazepan-1-yl)methanone

HRID 2204817
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2204817
Br[C:2]1[N:3]=[C:4]([C:9]2[S:10][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:12][N:13]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.C(OC([N:27]1[CH2:33][CH2:32][CH2:31][N:30]([C:34]([C:36]2[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=2)=[O:35])[CH2:29][CH2:28]1)=O)(C)(C)C.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl-].[Na+].O.CCOC(C)=O.O1CCOCC1>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:39]2[CH:38]=[CH:37][C:36]([C:34]([N:30]3[CH2:31][CH2:32][CH2:33][NH:27][CH2:28][CH2:29]3)=[O:35])=[CH:41][CH:40]=2)=[N:3][C:4]=1[C:9]1[S:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:12][N:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 594718915-Bromo-3-(5-phenyl-1,3,4-thiadiazol-2-yl)pyrazin-2-amineHCID 68497265[4-(4-Tert-butoxycarbonyl-1,4-diazepane-1-carbonyl)phenyl]boronic acid

Produkt 1

HCID 59472181(4-(5-Amino-6-(5-phenyl-1,3,4-thiadiazol-2-yl)pyrazin-2-yl)phenyl)(1,4-diazepan-1-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

5-bromo-3-(5-phenyl-1,3,4-thiadiazol-2-yl)pyrazin-2-amine (70 mg, 0.1257 mmol) and [4-(4-tert-butoxycarbonyl-1,4-diazepane-1-carbonyl)phenyl]boronic acid (43.77 mg, 0.1257 mmol) (60% pure) were taken into dioxane (700.1 μL treated with Na2CO3 (125.7 μL of 2 M, 0.2514 mmol) and degassed/nitrogen flushed (5×). The reaction was then treated with palladium; triphenylphosphane (14.53 mg, 0.01257 mmol), degassed again and heated in the microwave at 140° C. for 30 minutes. The reaction was treated with EtOAc and brine, the organics separated, dried over MgSO4, filtered and concentrated under vacuum. The product was purified by column chromatography eluting 50% EtOAc/Petroleum ether followed by 10% MeOH/DCM to give the desired product which was dissolved in DCM (2.000 mL) and treating with TFA (2.960 g, 2.000 mL, 25.96 mmol). After stirring at RT for 30 minutes and concentration, the residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 mM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, passed through a sodium bicarbonate cartridge and freeze-dried to give the title compound (42 mg, 74% Yield). 1H NMR (400.0 MHz, DMSO) d 1.60 (1H, m), 1.77 (1H, m), 2.72-2.39 (4H, m_, 3.40 (2H, m), 3.60-3.67 (2H, m), 7.52 (2H, d), 7.58-7.65 (3H, m), 7.99 (1H, m), 8.00 (2H, br s), 8.10-8.14 (3H, m), 8.95 (1H, s); MS (ES+) 458.07

Aufarbeitung

  1. customdegassed/nitrogen
  2. customflushed (5×)
  3. additionThe reaction was then treated with palladium
  4. dry with materialthe organics separated, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe product was purified by column chromatography
  8. washeluting 50% EtOAc/Petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-3fe09537b24b4cbfb1660b76e3d3ff0c
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09365557B2

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