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37.ii
ii) 4-(l,4-dioxaspiro[4.51dec-8-vDaniline; Palladium (10 wt. %) on carbon (1.0 g) was added in one portion to a solution of benzyl N- [4-(l,4-dioxaspiro[4.5]dec-7-en-8-yl)phenyl]carbamate (7.01 g, 19.20 mmol) in THF (500 mL) and the reaction mixture was stirred under a hydrogen atmosphere at ambient temperature for 16 h. The reaction mixture was filtered and concentrated in vacuo to leave the title compound as a white solid (4.03 g, 90%). 1H NMR δ 1.51 - 1.76 (m, 8H), 2.32 - 2.43 (m, IH), 3.87 (s, 4H), 4.77 (s, 2H), 6.48 (d, 2H), 6.86 (d, 2H).
With potassium carbonate In N,N-dimethyl acetamide at 60℃; for 16h;
37.iii
iii) iyjV-Dibenzyl-4-(l,4-dioxaspiro[4.51dec-8-v0aniliiie; Benzyl bromide (5.95 g, 34.80 mmol) was added to a solution of 4-(l,4- dioxaspiro[4.5]dec-8-yl)aniline (3.87 g, 16.57 mmol) and potassium carbonate (6.86 g, 49.71 mmol) in DMA (60 mL) and stirred under a nitrogen atmosphere at 60°C for 16 h. The reaction mixture was allowed to cool to ambient temperature and water (30 mL) was added. The resulting precipitate was removed by filtration and dried under high vacuum to give the title compound as a white solid (5.46 g, 85%).1H NMR δ 1.46 - 1.77 (m, 8H), 2.32 - 2.46 (m, IH), 3.84 (s, 4H), 4.63 (s, 4H), 6.58 (d, 2H), 6.92 (d, 2H), 7.16 - 7.36 (m, 10H); MS m/e MH+ 414.
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In <i>N</i>-methyl-acetamide
130 N-[4-(1,4-Dioxa-spiro[4.5]dec-8-yl)-phenyl]-3-(4'-trifluoromethylbiphenyl-2-carbonylamino)-benzoic acid amide
EXAMPLE 130 N-[4-(1,4-Dioxa-spiro[4.5]dec-8-yl)-phenyl]-3-(4'-trifluoromethylbiphenyl-2-carbonylamino)-benzoic acid amide Prepared analogously to Example 34 from 3-(4'-trifluoromethyl-biphenyl-2-carbonylamino)-benzoic acid, 4-(1,4-dioxa-spiro[4.5]dec-8-yl)-phenylamine, TBTU and N-ethyldiisopropylamine in dimethylformamide. Yield:90% of theory Rf value:0.77 (silica gel; dichloromethane/ethanol=9:1)
trans-3-[4-[2-[5-[(4-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl]-1H-benzoimidazol-5-yl]cyclohexyl]oxypropanoic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 13 steps
1.1: potassium carbonate / N,N-dimethyl acetamide / 16 h / 60 °C
2.1: water; trifluoroacetic acid / 72 h / 20 °C
3.1: sodium tetrahydroborate / ethanol; acetonitrile / 1 h / 20 °C
3.2: 0.25 h / 20 °C
4.1: sodium hydroxide; water; tetra(n-butyl)ammonium hydrogensulfate / dichloromethane / 16 h / 20 °C
5.1: hydrogenchloride / water / 4 h / 70 °C
6.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 16 h / 20 °C
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C
8.1: ammonium nitrate; trifluoroacetic anhydride / dichloromethane / 2.52 h / 0 - 20 °C
9.1: hydrazine / ethanol / 1 h / 60 °C
10.1: N,N-dimethyl-formamide / 1 h / 60 °C
10.2: 4 h / 85 °C
11.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 16 h / 20 °C
12.1: acetic acid / 0.25 h / 100 °C / microwave irradiation
13.1: methanol; sodium hydroxide; water / tetrahydrofuran / 6 h / 20 °C
13.2: 0 °C
methyl trans-3-[4-[3-amino-4-[[5-[(4-fluorophenyl)amino]-1,3,4-oxadiazole-2-carbonyl]amino]phenyl]cyclohexyl]oxypropanoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 11 steps
1.1: potassium carbonate / N,N-dimethyl acetamide / 16 h / 60 °C
2.1: water; trifluoroacetic acid / 72 h / 20 °C
3.1: sodium tetrahydroborate / ethanol; acetonitrile / 1 h / 20 °C
3.2: 0.25 h / 20 °C
4.1: sodium hydroxide; water; tetra(n-butyl)ammonium hydrogensulfate / dichloromethane / 16 h / 20 °C
5.1: hydrogenchloride / water / 4 h / 70 °C
6.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 16 h / 20 °C
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C
8.1: ammonium nitrate; trifluoroacetic anhydride / dichloromethane / 2.52 h / 0 - 20 °C
9.1: hydrazine / ethanol / 1 h / 60 °C
10.1: N,N-dimethyl-formamide / 1 h / 60 °C
10.2: 4 h / 85 °C
11.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 16 h / 20 °C
methyl trans-3-[4-[4-[[5-[(4-fluorophenyl)amino]-1,3,4-oxadiazole-2-carbonyl]amino]-3-nitro-phenyl]cyclohexyl]oxypropanoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 10 steps
1.1: potassium carbonate / N,N-dimethyl acetamide / 16 h / 60 °C
2.1: water; trifluoroacetic acid / 72 h / 20 °C
3.1: sodium tetrahydroborate / ethanol; acetonitrile / 1 h / 20 °C
3.2: 0.25 h / 20 °C
4.1: sodium hydroxide; water; tetra(n-butyl)ammonium hydrogensulfate / dichloromethane / 16 h / 20 °C
5.1: hydrogenchloride / water / 4 h / 70 °C
6.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 16 h / 20 °C
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C
8.1: ammonium nitrate; trifluoroacetic anhydride / dichloromethane / 2.52 h / 0 - 20 °C
9.1: hydrazine / ethanol / 1 h / 60 °C
10.1: N,N-dimethyl-formamide / 1 h / 60 °C
10.2: 4 h / 85 °C
Multi-step reaction with 6 steps
1.1: potassium carbonate / N,N-dimethyl acetamide / 16 h / 60 °C
2.1: water; trifluoroacetic acid / 72 h / 20 °C
3.1: sodium tetrahydroborate / ethanol; acetonitrile / 1 h / 20 °C
3.2: 0.25 h / 20 °C
4.1: sodium hydroxide; water; tetra(n-butyl)ammonium hydrogensulfate / dichloromethane / 16 h / 20 °C
5.1: hydrogenchloride / water / 4 h / 70 °C
6.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 16 h / 20 °C
Multi-step reaction with 3 steps
1.1: potassium carbonate / N,N-dimethyl acetamide / 16 h / 60 °C
2.1: water; trifluoroacetic acid / 72 h / 20 °C
3.1: sodium tetrahydroborate / ethanol; acetonitrile / 1 h / 20 °C
3.2: 0.25 h / 20 °C
Multi-step reaction with 7 steps
1.1: potassium carbonate / N,N-dimethyl acetamide / 16 h / 60 °C
2.1: water; trifluoroacetic acid / 72 h / 20 °C
3.1: sodium tetrahydroborate / ethanol; acetonitrile / 1 h / 20 °C
3.2: 0.25 h / 20 °C
4.1: sodium hydroxide; water; tetra(n-butyl)ammonium hydrogensulfate / dichloromethane / 16 h / 20 °C
5.1: hydrogenchloride / water / 4 h / 70 °C
6.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 16 h / 20 °C
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C
Multi-step reaction with 5 steps
1.1: potassium carbonate / N,N-dimethyl acetamide / 16 h / 60 °C
2.1: water; trifluoroacetic acid / 72 h / 20 °C
3.1: sodium tetrahydroborate / ethanol; acetonitrile / 1 h / 20 °C
3.2: 0.25 h / 20 °C
4.1: sodium hydroxide; water; tetra(n-butyl)ammonium hydrogensulfate / dichloromethane / 16 h / 20 °C
5.1: hydrogenchloride / water / 4 h / 70 °C
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