2-Bromo-6-phenylcyclohexanone → N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-2-amine

HRID 1803261

Reaktionsgleichung

Reaktionsgleichung von HRID 1803261
Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]1=O.[Cl:15][C:16]1[N:17]=[CH:18][N:19]([C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH2:30])=[S:29])=[CH:23][C:22]=2[O:31][CH3:32])[CH:20]=1>C(O)C.CCOC(C)=O>[Cl:15][C:16]1[N:17]=[CH:18][N:19]([C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]3[S:29][C:2]4[CH2:7][CH2:6][CH2:5][CH:4]([C:8]5[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=5)[C:3]=4[N:30]=3)=[CH:23][C:22]=2[O:31][CH3:32])[CH:20]=1

Komponenten

5

Edukt 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 866498881-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)thiourea

Produkt 1

HCID 58110069N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-2-amineAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2-bromo-6-phenylcyclohexanone (89 mg, 0.352 mmol, from preparation AAA) and 1-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)thiourea (99 mg, 0.352 mmol, from step 4 of preparation A) was heated in ethanol (0.60 mL) at 80° C. for 3 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 (60% acetone/hexanes) to give 42 mg (26% yield) of the titled compound as a white solid. LC-MS (M+H)+ 437.0. 1H NMR (400 MHz, chloroform-d) δ ppm 7.50 (d, J=1.51 Hz, 1 H) 7.45 (d, J=2.52 Hz, 1 H) 7.28-7.36 (m, 2 H) 7.14-7.23 (m, 3H) 7.08 (d, J=8.31 Hz, 1 H) 7.00 (d, J=1.51 Hz, 1 H) 6.60 (dd, J=8.44, 2.39 Hz, 1 H) 4.05 (t, J=6.30 Hz, 1H) 3.47 (s, 3 H) 2.68-2.89 (m, 2 H) 2.20-2.28 (m, 1 H) 1.98 (dd, J=7.30, 5.29 Hz, 1 H) 1.78-1.93 (m, 2 H).

Aufarbeitung

  1. customfrom step 4 of preparation A)
  2. customThe crude reaction
  3. washwashed with saturated sodium bicarbonate solution
  4. concentrationThe organic layer was concentrated in vacuo
  5. customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-3cee49f658c345d3b3b0ef7a4d9fc464
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349880B2

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