Potassium Carbonate → tert-butyl 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazol-6-yl-carbamate

HRID 516303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516303
[F:1][CH:2]([F:22])[C:3]1[NH:7][C:6]2[CH:8]=[C:9]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:10]=[C:11]([O:12][CH3:13])[C:5]=2[N:4]=1.[Cl:23][C:24]1[N:29]=[C:28](Cl)[N:27]=[C:26]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[N:25]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:23][C:24]1[N:25]=[C:26]([N:31]2[CH2:32][CH2:33][O:34][CH2:35][CH2:36]2)[N:27]=[C:28]([N:7]2[C:6]3[CH:8]=[C:9]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH:10]=[C:11]([O:12][CH3:13])[C:5]=3[N:4]=[C:3]2[CH:2]([F:1])[F:22])[N:29]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 810762,4-Dichloro-6-morpholino-1,3,5-triazineHCID 66698048tert-butyl 2-(difluoromethyl)-4-methoxy-1H-benzimidazol-6-yl-carbamate

Produkt 1

HCID 86645852tert-butyl 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazol-6-yl-carbamateAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 2-(difluoromethyl)-4-methoxy-1H-benzimidazol-6-yl-carbamate (0.47 g, 1.5 mmol), 2,4-dichloro-6-(4-morpholinyl)-1,3,5-triazine (0.35 g, 1.5 mmol), and powdered K2CO3 (0.83 g, 6 mmol) in DMF (10 mL) was stirred at room temperature for 30 min. The reaction mixture was then diluted with water. The resulting precipitate was collected, washed with water and then MeOH, and dried to give 0.45 g (59% yield) of tert-butyl 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazol-6-yl-carbamate: mp (CH2Cl2/MeOH)>300° C.; 1H NMR (CDCl3) δ 8.45 (d, J=0.6 Hz, 1H), 7.57 (t, JHF=53.6 Hz, 1H), 6.67 (br, exchangeable with D2O, 1H), 6.63 (d, J=0.9 Hz, 1H), 4.11 (m, 2H), 4.02 (s, 3H), 3.97 (m, 2H), 3.88 (m, 2H), 3.82 (m, 2H), 1.52 (s, 9H); Anal. Calcd. for C21H24ClF2N7O4: C, 49.3; H, 4.7; N, 19.15. Found: C, 49.4; H, 4.8; N, 19.2%.

Aufarbeitung

  1. customThe resulting precipitate was collected
  2. washwashed with water
  3. dry with materialMeOH, and dried

Quellen und Nachweise

ORD-Eintrag
ord-0855f00490be44e082141466387e8d0b
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108980B2

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