Formaldehyde → 6,6-Dimethyl-2-{6-[n-methyl-n-(6-methylpyridin-3-yl)amino]-2,3-dihydro-4h-1,4-benzoxazin-4-yl}-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

HRID 885971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 885971
[CH3:1][C:2]1([CH3:30])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[C:19]([NH:22][C:23]5[CH:24]=[N:25][C:26]([CH3:29])=[CH:27][CH:28]=5)[CH:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1.C=O.[CH2:33]([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>C1COCC1>[CH3:1][C:2]1([CH3:30])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[C:19]([N:22]([CH3:33])[C:23]5[CH:24]=[N:25][C:26]([CH3:29])=[CH:27][CH:28]=5)[CH:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1

Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 671856026,6-Dimethyl-2-[6-(6-methylpyridin-3-ylamino)-2,3-dihydrobenzo[1,4]oxazin-4-yl]-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

Produkt 1

HCID 671903716,6-Dimethyl-2-{6-[n-methyl-n-(6-methylpyridin-3-yl)amino]-2,3-dihydro-4h-1,4-benzoxazin-4-yl}-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-oneAusbeute 1.148 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred solution of Example 60 (0.017 g, 0.04 mmol), paraformaldehyde (0.04 g, 0.28 mmol), dibutyltin dichloride (0.0015 g, 0.004 mmol) and phenyl silane (0.01 g, 0.08 mmol) in THF (4 mL) was heated to 100° C. under microwave irradiation in a sealed tube for 1 h. The reaction mixture was concentrated in vacuo. Purification by preparative HPLC (Method 7) gave the title compound (0.020 g, 34%) as an off-white solid. δH (CDCl3) 8.20 (1H, d, J 2.8 Hz), 7.70 (1H, d, J 2.5 Hz), 7.16 (1H, d, J 8.5 Hz), 7.05-6.99 (1H, m), 6.93-6.87 (1H, m), 6.78 (1H, dd, J 8.7 and 2.5 Hz), 5.15 (1H, s), 4.36-4.29 (2H, m), 4.18-4.10 (2H, m), 3.20 (3H, s), 2.80 (2H, s), 2.50 (3H, s), 1.40 (6H, s). LCMS (ES+) 436 (M+H)+, RT 3.30 minutes (Method 2).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customPurification by preparative HPLC (Method 7)

Quellen und Nachweise

ORD-Eintrag
ord-c3ff64e86f364a3eb73c2d7de2a721ee
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242116B2

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