3-Bromocyclohexane-1,2-dione → 2-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-6,7-dihydrobenzo[d]thiazol-4(5H)-one

HRID 1803269Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1803269
Br[CH:2]1[CH2:7][CH2:6][CH2:5][C:4](=O)[C:3]1=[O:9].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([NH:24][C:25]([NH2:27])=[S:26])[CH:15]=[CH:16][C:17]=1[N:18]1[CH:22]=[N:21][C:20]([CH3:23])=[N:19]1>C(O)C.CCOC(C)=O>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([NH:24][C:25]2[S:26][C:7]3[CH2:6][CH2:5][CH2:4][C:3](=[O:9])[C:2]=3[N:27]=2)[CH:15]=[CH:16][C:17]=1[N:18]1[CH:22]=[N:21][C:20]([CH3:23])=[N:19]1

Komponenten

5

Edukt 2

HCID 134385013-Bromocyclohexane-1,2-dioneHCID 866498981-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea

Produkt 1

HCID 866499272-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-6,7-dihydrobenzo[d]thiazol-4(5H)-oneAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3-bromocyclohexane-1,2dione (158 mg, 0.827 mmol, from preparation AAE) and 1-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea (109 mg, 0.414 mmol, from step 4 of preparation F) was heated in ethanol (1.4 mL) at 80° C. for 12 h. The crude reaction was diluted with EtOAc and washed with saturated sodium bicarbonate solution. The organic layer was concentrated in vacuo. The crude product was purified using preparatory TLC (80% acetone/hexanes) to afford 2-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-6,7-dihydrobenzo[d]thiazol-4(5H)-one (64 mg, 44% yield) as a yellow solid. LC-MS (M+H)+ 356.3. 1H NMR (400 MHz, chloroform-d) δ ppm 8.55 (s, 1 H) 7.68 (d, J=8.56 Hz, 1 H) 7.31 (d, J=2.27 Hz, 1 H) 6.96 (dd, J=8.56, 2.52 Hz, 1 H) 3.95 (s, 3H) 3.00 (t, J=6.04 Hz, 2 H) 2.59-2.68 (m, 2 H) 2.45-2.52 (m, 3H) 2.20-2.31 (m, 2H).

Aufarbeitung

  1. customThe crude reaction
  2. washwashed with saturated sodium bicarbonate solution
  3. concentrationThe organic layer was concentrated in vacuo
  4. customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-6c147d0da6944f0491aa71fe5b00fe1a
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349880B2

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