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

HRID 885981
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 885981
[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+].Br[C:39]1[N:40]=[C:41]([CH3:45])[N:42]([CH3:44])[CH:43]=1>C1COCC1.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:44][N:42]1[CH:43]=[C:39]([C:19]2[CH:20]=[CH:21][C:16]3[O:15][CH2:14][CH2:13][N:12]([C:10]4[S:9][C:5]5[C:6](=[O:8])[NH:7][C:2]([CH3:31])([CH3:1])[CH2:3][C:4]=5[N:11]=4)[C:17]=3[CH:18]=2)[N:40]=[C:41]1[CH3:45]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 72048754-Bromo-1,2-dimethyl-1H-imidazoleHCID 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 671880512-[6-(1,2-Dimethyl-1h-imidazol-4-yl)-2,3-dihydro-4h-1,4-benzoxazin-4-yl]-6,6-dimethyl-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-oneAusbeute 14,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of Example 292 (75 mg, 0.17 mmol) in THF (3 mL) and water (1 mL) was added tetra-n-butylammonium bromide (107 mg, 0.34 mmol), sodium carbonate (36 mg, 0.34 mmol), 4-bromo-1,2-dimethyl-1H-imidazole (60 mg, 0.34 mmol) and tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol). The reaction was heated at 140° C. under microwave irradiation for 25 minutes. The resulting mixture was partitioned between DCM (50 mL) and water (50 mL); the organic fraction 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 (10 mg, 14%) as an off-white solid. δH (CDCl3) 8.09 (1H, d, J 2.1 Hz), 7.48 (1H, dd, J 8.5 and 2.1 Hz), 7.02 (1H, s), 6.95 (1H, d, J 8.5 Hz), 5.22 (1H, br. s), 4.36-4.29 (2H, m), 4.24-4.19 (2H, m), 3.60 (3H, s), 2.88 (2H, s), 2.42 (3H, s), 1.40 (6H, s). LCMS (ES+) 410.0 (M+H)+, RT 1.86 minutes (Method 1).

Aufarbeitung

  1. customThe resulting mixture was partitioned between DCM (50 mL) and water (50 mL)
  2. washthe organic fraction 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-48e18104b8c24bbe983ad6f36126d4d6
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08242116B2

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