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Sodium Carbonate → 6,6-Dimethyl-2-(6-(pyrazin-2-yl)-2,3-dihydro-4h-1,4-benzoxazin-4-yl)-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

HRID 885980
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 885980
[CH3:1][C:2]1([CH3:31])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[C:19](B5OC(C)(C)C(C)(C)O5)[CH:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1.C(=O)([O-])[O-].[Na+].[Na+].I[C:39]1[CH:44]=[N:43][CH:42]=[CH:41][N:40]=1>C1COCC1.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][C:2]1([CH3:31])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[C:19]([C:39]5[CH:44]=[N:43][CH:42]=[CH:41][N:40]=5)[CH:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1
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Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 642841IodopyrazineHCID 584916876,6-dimethyl-2-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one

Produkt 1

HCID 671861206,6-Dimethyl-2-(6-(pyrazin-2-yl)-2,3-dihydro-4h-1,4-benzoxazin-4-yl)-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-oneAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of Example 292 (60 mg, 0.167 mol) in THF (3 mL) and water (1 mL) was added tetra-n-butylammonium bromide (107 mg, 0.334 mmol), sodium carbonate (36 mg, 0.334 mmol), iodopyrazine (69 mg, 0.509 mmol) and tetrakis-(triphenylphosphine)palladium(0) (19 mg, 0.017 mmol). The reaction was heated at 120° C. under microwave irradiation for 20 minutes. The resulting mixture was partitioned between DCM (50 mL) and water (50 mL); the organic phase was washed with brine (50 mL), dried (MgSO4), and concentrated in vacuo. The residue was purified by preparative HPLC (Method 6) to yield the title compound (15 mg, 23%) as an off-white solid. δH (CDCl3) 9.00 (1H, s), 8.75 (1H, d, J 2.1 Hz), 8.60 (1H, dd, J 2.4 and 1.7 Hz), 8.48 (1H, d, J 2.4 Hz), 7.74 (1H, dd, J 8.5 and 2.1 Hz), 7.09 (1H, d, J 8.7 Hz), 5.34 (1H, s), 4.43-4.39 (2H, m), 4.22-4.18 (2H, m), 2.90 (2H, s), 1.41 (6H, s). LCMS (ES+) 394.0 (M+H)+, RT 2.93 minutes (Method 1).

Aufarbeitung

  1. customThe resulting mixture was partitioned between DCM (50 mL) and water (50 mL)
  2. washthe organic phase was washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC (Method 6)

Quellen und Nachweise

ORD-Eintrag
ord-b12c6933caf849cc811956df445316fd
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08242116B2

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