p-(Trifluoromethoxy)phenyl isocyanate → [4-(4-{5-[3-(4-Trifluoromethoxy-phenyl)-ureido]-pyridin-2-yl)-phenyl)-cyclohexyl]-acetic acid

HRID 76066

Reaktionsgleichung

Reaktionsgleichung von HRID 76066
C[O:2][C:3](=[O:24])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][N:18]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[N:25]([C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=1)=[C:26]=[O:27]>C(Cl)Cl>[F:36][C:35]([F:37])([F:38])[O:34][C:31]1[CH:30]=[CH:29][C:28]([NH:25][C:26](=[O:27])[NH:23][C:20]2[CH:21]=[CH:22][C:17]([C:14]3[CH:15]=[CH:16][C:11]([CH:8]4[CH2:9][CH2:10][CH:5]([CH2:4][C:3]([OH:2])=[O:24])[CH2:6][CH2:7]4)=[CH:12][CH:13]=3)=[N:18][CH:19]=2)=[CH:33][CH:32]=1

Komponenten

4

Edukt 2

HCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 66615773Methyl 2-((1r,4r)-4-(4-(5-aminopyridin-2-yl)phenyl)cyclohexyl)acetate

Produkt 1

HCID 57899110[4-(4-{5-[3-(4-Trifluoromethoxy-phenyl)-ureido]-pyridin-2-yl)-phenyl)-cyclohexyl]-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To 150 mg (0.5 mmol) {4-[4-(5-Amino-pyridin-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester in 5 mL DCM, 102 mg (0.5 mmol) 1-Isocyanato-4-trifluoromethoxy-benzene was added and the resulting mixture was stirred at room temperature over night. Dilution of reaction mixture with hexanes caused desired product to precipitate which was collected by filtration to afford [4-(4-{5-[3-(4-Trifluoromethoxy-phenyl)-ureido]-pyridin-2-yl}-phenyl)-cyclohexyl]-acetic acid methyl ester: M+1=528.2. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.09-1.20 (m, 2H) 1.50 (td, J=112.63, 10.11 Hz, 2H) 1.80 (s, 3H) 1.83 (d, J=3.28 Hz, 2H) 2.25 (d, J=6.82 Hz, 2H) 2.51-2.54 (m, 1H) 3.61 (s, 3H) 7.31 (dd, J=8.72, 3.16 Hz, 4H) 7.55-7.61 (m, 2H) 7.86 (d, J=8.59 Hz, 1H) 7.94 (d, J=8.34 Hz, 2H) 8.02 (dd, J=8.72, 2.65 Hz, 1H) 8.66 (d, J=2.78 Hz, 1H) 8.99 (s, 1H) 9.05 (s, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-34a91b0fdc8a48a8b094e11ce277d330
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835451B2

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