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[ CAS No. 17647-70-0 ] {[proInfo.proName]}

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Product Details of [ 17647-70-0 ]

CAS No. :17647-70-0 MDL No. :MFCD00186403
Formula : C3H5N3O Boiling Point : -
Linear Structure Formula :- InChI Key :QIEJLLIYONRHBH-UHFFFAOYSA-N
M.W : 99.09 Pubchem ID :28674
Synonyms :

Calculated chemistry of [ 17647-70-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.33
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 23.67
TPSA : 64.94 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.09
Log Po/w (XLOGP3) : 0.09
Log Po/w (WLOGP) : -0.03
Log Po/w (MLOGP) : -0.76
Log Po/w (SILICOS-IT) : 0.37
Consensus Log Po/w : 0.15

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.04
Solubility : 9.04 mg/ml ; 0.0913 mol/l
Class : Very soluble
Log S (Ali) : -1.01
Solubility : 9.72 mg/ml ; 0.0981 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.81
Solubility : 15.2 mg/ml ; 0.153 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.58

Safety of [ 17647-70-0 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 17647-70-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 17647-70-0 ]

[ 17647-70-0 ] Synthesis Path-Downstream   1~96

  • 1
  • [ 17647-70-0 ]
  • [ 108-24-7 ]
  • [ 65225-88-9 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate
  • 2
  • [ 17647-70-0 ]
  • [ 100-52-7 ]
  • <i>N</i>,<i>N</i>'-bis-(4-methyl-furazan-3-yl)-benzylidenediamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide
  • 3
  • [ 17647-70-0 ]
  • [ 104-55-2 ]
  • cinnamylidene-(methyl-furazan-3-yl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ethanol
  • 5
  • [ 17647-70-0 ]
  • 1,3-bis(4-methylfurazanyl)triazene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium nitrite
With sulfuric acid; sodium nitrite
With phosphoric acid; sulfuric acid; sodium nitrite 1.) 0-2 deg C, 1 h, 2.) H2O, 0 deg C; Yield given. Multistep reaction;
  • 7
  • [ 31915-82-9 ]
  • [ 17647-70-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium hydroxide; hydroxylamine
  • 8
  • [ 17647-70-0 ]
  • [ 103-71-9 ]
  • [ 63558-48-5 ]
YieldReaction ConditionsOperation in experiment
at 100℃;
  • 9
  • [ 17647-70-0 ]
  • [ 103-72-0 ]
  • [ 64821-98-3 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide
In Petroleum ether; benzene 10 Preparation of N-(4-methylfurazan-3-yl)-N'-phenylthiourea Example 10 Preparation of N-(4-methylfurazan-3-yl)-N'-phenylthiourea 2.5 g (about 0.025 moles) of 4-methyl-3-aminofurazan, 6 ml di dimethylformamide, 3.4 g of phenylisothiocyanate and traces of hydrochloric acid as a catalyst are loaded into a glass flask fitted with a sealed stopper. The flask is closed and placed in an oven at 30°C for 40 hours. The reaction mixture is poured into cold water under agitation. The precipitate is filtered and dissolved in a little benzene. The benzene solution is filtered and petroleum ether is added to the filtrate causing the precipitation of a solid which is crystallized from ethanol, giving 2 g of crystals of the title product, with a melting point of 124-125°C (crystallized from ethanol).
  • 10
  • [ 17647-70-0 ]
  • [ 79-04-9 ]
  • [ 32545-22-5 ]
YieldReaction ConditionsOperation in experiment
77% In tetrahydrofuran
With sodium acetate In acetic acid
  • 11
  • [ 306-44-5 ]
  • [ 17647-70-0 ]
YieldReaction ConditionsOperation in experiment
81% With sodium hydroxide; hydroxylamine hydrochloride; urea In water for 3h; Heating;
With potassium hydroxide; hydroxylamine hydrochloride Heating;
  • 12
  • [ 17647-70-0 ]
  • [ 612-62-4 ]
  • (4-Methyl-furazan-3-yl)-quinolin-2-yl-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% at 170℃; for 18h;
  • 13
  • [ 17647-70-0 ]
  • [ 4487-59-6 ]
  • (4-Methyl-furazan-3-yl)-(5-nitro-pyridin-2-yl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% at 170 - 190℃;
  • 14
  • [ 17647-70-0 ]
  • [ 50-00-0 ]
  • methylene-bis-(3-amino-4-methylfurazan) [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With hydrogenchloride In water for 0.0833333h; Heating;
85% With sulfuric acid for 1h; Ambient temperature;
  • 15
  • [ 17647-70-0 ]
  • [ 5470-18-8 ]
  • (4-Methyl-furazan-3-yl)-(3-nitro-pyridin-2-yl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% at 170 - 190℃;
  • 16
  • [ 17647-70-0 ]
  • [ 15679-03-5 ]
  • [ 130137-89-2 ]
YieldReaction ConditionsOperation in experiment
78% 1.) 110 deg C, 1 h, 2.) 160 deg C, 1 h;
  • 17
  • [ 17647-70-0 ]
  • [ 459-57-4 ]
  • [ 868-85-9 ]
  • [(4-Fluoro-phenyl)-(4-methyl-furazan-3-ylamino)-methyl]-phosphonic acid dimethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With dibenzo-24-crown ether In benzene for 4h; Heating;
  • 18
  • [ 17647-70-0 ]
  • [ 100-07-2 ]
  • [ 147188-74-7 ]
YieldReaction ConditionsOperation in experiment
With pyridine In benzene
  • 19
  • [ 17647-70-0 ]
  • [ 16182-04-0 ]
  • [ 109610-14-2 ]
YieldReaction ConditionsOperation in experiment
60% In N,N-dimethyl-formamide for 24h; Ambient temperature;
  • 20
  • [ 17647-70-0 ]
  • [ 625-36-5 ]
  • [ 115173-96-1 ]
YieldReaction ConditionsOperation in experiment
81% In tetrahydrofuran
  • 23
  • [ 1804-15-5 ]
  • [ 17647-70-0 ]
YieldReaction ConditionsOperation in experiment
63% With sodium hydroxide; hydroxylamine hydrochloride In water for 3h; Heating;
  • 24
  • [ 137890-25-6 ]
  • [ 17647-70-0 ]
YieldReaction ConditionsOperation in experiment
40% With potassium hydroxide for 144h; Ambient temperature;
  • 25
  • [ 137890-19-8 ]
  • [ 17647-70-0 ]
YieldReaction ConditionsOperation in experiment
46% With potassium hydroxide In ethanol for 2h; Heating;
  • 26
  • [ 17647-70-0 ]
  • [ 37101-10-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; phosphoric acid; sulfuric acid; copper(l) chloride; sodium nitrite 1.) 0-2 deg C, 1 h, 2.) 1 h; Yield given. Multistep reaction;
  • 27
  • [ 17647-70-0 ]
  • [ 77580-81-5 ]
YieldReaction ConditionsOperation in experiment
35% With sodium nitrite In dichloromethane; acetonitrile at 20℃;
With phosphoric acid; sulfuric acid; sodium iodide; sodium nitrite 1.) 0-2 deg C, 1 h, 2.) H2O; Yield given. Multistep reaction;
  • 28
  • [ 17647-70-0 ]
  • [ 77666-53-6 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 3-amino-4-methylfurazan With sodium nitrite In dimethyl sulfoxide at 0 - 2℃; for 0.333333h; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 0 - 2℃; for 2.5h;
83% With sodium tungstate (VI) dihydrate; dihydrogen peroxide; acetic acid at 40 - 70℃; for 1.5h; Preparation of 3-alkyl-4-nitrofurazans 1a-f General procedure: (Generalmethod). A solution of amine 2a-f (70.84 mmol) in AcOH(70 ml) was added dropwise to a solution of Na2WO4·2H2O(23.37 g, 70.84 mmol) in 37% H2O2 (250 ml) heated to 40°.The reaction mixture was then heated to 70° and stirred atthis temperature for 1.5 h, cooled to 50°, and poured intoa mixture of ice (100 g) and water (100 ml). The obtainedsolution was extracted with CH2Cl2 (3×100 ml). Thecombined extracts were washed with water (2×100 ml) anddried over anhydrous MgSO4. The solvent was removed byevaporation and the residue was purified by distillation.3-Methyl-4-nitrofurazan (1a). Yield 83%, light-yellowoil, bp 65° (16 mmHg). NMR spectral data wereanalogous to those previously reported in the literature.6
With phosphoric acid; sulfuric acid; dinitrogen tetraoxide; copper; sodium nitrite 1.) 0-2 deg C, 1 h, 2.) below 10 deg C, 12 h; Yield given. Multistep reaction;
  • 29
  • [ 17647-70-0 ]
  • 3-azido-4-methylfurazan [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium azide; phosphoric acid; sulfuric acid; sodium nitrite 1.) 0-2 deg C, 1 h, 2.) H2O, 0 deg C; Yield given. Multistep reaction;
YieldReaction ConditionsOperation in experiment
With hydrogenchloride
YieldReaction ConditionsOperation in experiment
With hydrogenchloride
  • 32
  • [ 17647-70-0 ]
  • [ 2251-50-5 ]
  • [ 361448-17-1 ]
YieldReaction ConditionsOperation in experiment
70% With pyridine In benzene at 20℃; for 24h;
  • 33
  • [ 17647-70-0 ]
  • [ 612-29-3 ]
  • 2-(4-methylfurazan-3-yl)-1-(2-nitrophenyl)diazene 1-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dibromoisocyanuric acid In acetonitrile at 20℃; for 5h;
  • 34
  • [ 696-59-3 ]
  • [ 17647-70-0 ]
  • [ 473812-12-3 ]
YieldReaction ConditionsOperation in experiment
66.6% With acetic acid for 0.25h; Heating;
  • 35
  • [ 17647-70-0 ]
  • [ 56-23-5 ]
  • C4H3Cl2N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With 1-ethyl-3-methylimidazolium chloroaluminate at 80℃;
  • 37
  • [ 165816-78-4 ]
  • [ 17647-70-0 ]
  • 2-phenyltetrazol-2-ylacetic acid N-(4-methylfurazan-3-yl)amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With triethylamine In diethyl ether at 20℃;
  • 38
  • [ 306-44-5 ]
  • [ 17647-70-0 ]
  • [ 4937-85-3 ]
YieldReaction ConditionsOperation in experiment
15% With potassium hydroxide; hydroxylamine hydrochloride for 24h; Heating;
  • 39
  • [ 17647-70-0 ]
  • bis-(4-methyl-furazan-3-yl)-diazene <i>N</i>,<i>N</i>'-dioxide [ No CAS ]
  • [ 129282-35-5 ]
YieldReaction ConditionsOperation in experiment
With nitric acid; dinitrogen tetraoxide at -5 - 0℃;
  • 40
  • [ 17647-70-0 ]
  • 3-nitramino-4-methylfurazan [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With nitric acid; dinitrogen pentoxide
92% With nitric acid In water at 15 - 18℃; for 0.416667h;
  • 41
  • [ 17647-70-0 ]
  • bis-(4-methyl-furazan-3-yl)-diazene [ No CAS ]
  • 3-nitramino-4-methylfurazan [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With nitronium tetrafluoborate
  • 42
  • [ 17647-70-0 ]
  • [ 119915-43-4 ]
  • [ 122-51-0 ]
  • ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-(4-methyl-1,2,5-oxadiazol-3-ylamino)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic anhydride In chloroform 145 Ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-(4-methyl-1,2,5-oxadiazol-3-ylamino)acrylate (Compound No.223) EXAMPLE 145 Ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-(4-methyl-1,2,5-oxadiazol-3-ylamino)acrylate (Compound No.223) A mixture of ethyl 2-methyl-3,4,6-trifluorobenzoylacetate (2.6 g), ethyl orthoformate (2.5 ml) and acetic anhydride (2.8 ml) was stirred at 130° C. for 2 hours. After the solvent was removed in vacuo, a solution of 3-amino-4-methyl-1,2,5-oxadiazole (0.99 g) in chloroform(20 ml) was added to the residue. The mixture was stirred at room temperature for 24 hours. The solvent was removed. The residue was purified by chromatography on silicagel (chloroform as an eluent). The title compound No. 223 was obtained as a yellow oil (3.4 g). 1 H-NMR(CDCl3) δ; 1.01 and 1.16(t,J=7 Hz,3H), 2.22 and 2.28(d,J=2.2 Hz,3H), 2.46 and 2.51(s,3H), 4.05-4.2(m,2H), 6.7-6.9(m,1H), 8.62 and 8.79(d,J=12.6 Hz,1H)
  • 43
  • [ 17647-70-0 ]
  • [ 98349-24-7 ]
  • [ 122-51-0 ]
  • ethyl 3-(4-methyl-1,2,5-oxadiazol-3-ylamino)-2-(2,4,5-trifluorobenzoyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic anhydride; In chloroform; EXAMPLE 43 Ethyl 3-(4-methyl-1,2,5-oxadiazol-3-ylamino)-2-(2,4,5-trifluorobenzoyl)acrylate (Compound No.90) A mixture of <strong>[98349-24-7]ethyl 2,4,5-trifluorobenzoylacetate</strong> (2.46 g), ethyl orthoformate (2.6 ml) and acetic anhydride (2.8 ml) was stirred at 130 C. for 6 hours. After the solvent was removed in vacuo, a solution of 3-amino-4-methyl-1, 2,5-oxadiazole (1.04 g) in chloroform (10 ml) was added to the residue. The mixture was stirred at room temperature for 24 hours, then the solvent was removed. The residue was purified by chromatography on silicagel (chloroform as an eluent). The title compound No. 90 was obtained as a colorless solid (1.95 g). Melting point: 104-107 C. 1 H-NMR(CDCl3) delta; 1.05 and 1.20(t,J=7 Hz,3H), 2.45 and 2.48(s,3H), 4.1-4.3(m,2H), 6.85-7.0(m,1H), 7.3-7.41 and 7.48-7.6(m,1H), 8.39 and 8.69(q,J=12 Hz,1H)
  • 44
  • [ 17647-70-0 ]
  • [ 94695-50-8 ]
  • [ 122-51-0 ]
  • ethyl 2-(2,3,4,5-tetrafluorobenzoyl)-3-(4-methyl-1,2,5-oxadiazol-3-ylamino)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic anhydride; triethylamine; In chloroform; EXAMPLE 149 Ethyl 2-(2,3,4,5-tetrafluorobenzoyl)-3-(4-methyl-1,2,5-oxadiazol-3-ylamino)acrylate (Compound No.230) A mixture of ethyl 2,3,4,5-tetrafluorobenzoylacetate (1.06 g), ethyl orthoformate (1.2 ml) and acetic anhydride (1.3 ml) was stirred at 130 C. for 5 hours. After the solvent was removed in vacuo, a solution of 3-amino-4-methyl-1,2,5-oxadiazole (0.4 g) and triethylamine (0.4 g) in chloroform (10 ml) was added to the residue. The mixture was stirred at room temperature for 1 hour. The solvent was removed. The residue was-purified by chromatography on silicagel (chloroform/ethyl acetate 10:1 as an eluent). The title compound No. 230 was obtained as a pale yellow solid (1.17 g). Melting point: 88-92 C. 1 H-NMR(CDCl3) delta; 1.07 and 1.24(t,J=7 Hz,3H), 2.46 and 2.49(s,3H), 4.1-4.3(m,2H), 7.1-7.4(m,1H), 8.47 and 8.73 (d,J=12.6 Hz,1H)
  • 45
  • [ 17647-70-0 ]
  • ethyl 2,6-dichloro-5-fluoronicotinoylacetate [ No CAS ]
  • [ 122-51-0 ]
  • ethyl 3-(4-methyl-1,2,5-oxadiazol-3-ylamino)-2-(2,6-dichloro-5-fluoronicotinoyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic anhydride In chloroform 38 Ethyl 3-(4-methyl-1,2,5-oxadiazol-3-ylamino)-2-(2,6-dichloro-5-fluoronicotinoyl)acrylate (Compound No.77) EXAMPLE 38 Ethyl 3-(4-methyl-1,2,5-oxadiazol-3-ylamino)-2-(2,6-dichloro-5-fluoronicotinoyl)acrylate (Compound No.77) A mixture of ethyl 2,6-dichloro-5-fluoronicotinoylacetate (1.4 g), ethyl orthoformate (1.3 ml) and acetic anhydride (1.4 ml) was stirred at 130° C. for 17 hours. After the solvent was removed in vacuo, a solution of 3-amino-4-methyl-1,2,5-oxadiazole (545 mg) in chloroform (5 ml) was added to the residue. The mixture was stirred at room temperature for 24 hours. The solvent was removed and the residue was purified by chromatography on silicagel(chloroform as an eluent). The title compound No. 77 was obtained as a colorless solid (770 mg). Melting point: 139-141.5° C. 1 H-NMR(CDCl3) δ; 0.97 and 1.18(t,J=7 Hz,3H), 2.47 and 2.51(s,3H), 4.05-4.3(m,2H), 7.3 and 7.43(d,J=6.8 Hz,1H), 8.72 and 8.82(d,J=12.4 Hz,1H)
  • 46
  • [ 17647-70-0 ]
  • [ 110964-79-9 ]
  • N-(4-methyl-1,2,5-oxadiazol-3-yl)-4-(methylsulfonyl)-2-nitrobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With dmap; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In tetrahydrofuran; dichloromethane; at 20℃; for 30h; A. Chemical ExamplesSynthesis of N-(4-methyl-1,2,5-oxadiazol-3-yl)-4-(methylsulfonyl)-2-nitrobenzamide (example No. 1-18 in the tables)495 mg (2.02 mmol) of 2-nitro-4-methylsulfonylbenzoic acid and 200 mg (2.02 mmol) of 4-methyl-1,2,5-oxadiazol-3-ylamine are dissolved at room temperature (RT) in 5 ml of CH2Cl2 and treated with 0.28 ml (2.02 mmol) of triethylamine, 49 mg (0.40 mmol) of 4-dimethylaminopyridine (DMAP) and 1.93 g (3.03 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF). The reaction mixture is stirred for 30 h at RT and subsequently washed twice with in each case 5 ml of water. The organic phase is dried over Na2SO4 and evaporated. The residue is purified by column chromatography (silica gel, heptane/ethyl acetate). Yield 350 mg (53%).
  • 47
  • [ 17647-70-0 ]
  • [ 3173-56-6 ]
  • [ 1466-67-7 ]
  • [ 1393535-73-3 ]
  • [ 339243-28-6 ]
YieldReaction ConditionsOperation in experiment
60% In toluene at 170℃; for 0.333333h; Microwave irradiation;
  • 48
  • [ 17647-70-0 ]
  • [ 139308-14-8 ]
  • [ 1159781-71-1 ]
YieldReaction ConditionsOperation in experiment
41% With dibromoisocyanuric acid In dichloromethane at 20℃; for 2h;
  • 49
  • [ 374063-90-8 ]
  • [ 17647-70-0 ]
  • [ 100-52-7 ]
  • C18H13N3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: methyl 4-(furan-2-yl)-2,4-dioxobutanoate; 3-amino-4-methylfurazan; benzaldehyde With chloro-trimethyl-silane In N,N-dimethyl-formamide Sealed tube; Heating; Stage #2: With water In N,N-dimethyl-formamide at 20℃; for 2h; Sonication;
  • 50
  • [ 374063-90-8 ]
  • [ 17647-70-0 ]
  • [ 123-11-5 ]
  • C19H15N3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: methyl 4-(furan-2-yl)-2,4-dioxobutanoate; 3-amino-4-methylfurazan; 4-methoxy-benzaldehyde With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 51
  • [ 17647-70-0 ]
  • [ 123-11-5 ]
  • methyl 2,4-dioxo-4-(thiophen-2-yl)butanoate [ No CAS ]
  • C19H15N3O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-amino-4-methylfurazan; 4-methoxy-benzaldehyde; methyl 2,4-dioxo-4-(thiophen-2-yl)butanoate With chloro-trimethyl-silane In N,N-dimethyl-formamide Sealed tube; Heating; Stage #2: With water In N,N-dimethyl-formamide at 20℃; for 2h; Sonication;
  • 52
  • [ 17647-70-0 ]
  • [ 10031-82-0 ]
  • methyl 2,4-dioxo-4-(thiophen-2-yl)butanoate [ No CAS ]
  • C20H17N3O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-amino-4-methylfurazan; 4-ethoxybenzaldehyde; methyl 2,4-dioxo-4-(thiophen-2-yl)butanoate With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 53
  • [ 17647-70-0 ]
  • [ 10031-82-0 ]
  • [ 20577-61-1 ]
  • C17H17N3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-amino-4-methylfurazan; 4-ethoxybenzaldehyde; methyl 2,4-dioxopentanoate With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 54
  • [ 498-62-4 ]
  • [ 17647-70-0 ]
  • [ 167408-67-5 ]
  • C15H13N3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-thiophene carboxaldehyde; 3-amino-4-methylfurazan; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 55
  • [ 498-62-4 ]
  • [ 17647-70-0 ]
  • [ 20577-61-1 ]
  • C13H11N3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-thiophene carboxaldehyde; 3-amino-4-methylfurazan; methyl 2,4-dioxopentanoate With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 56
  • [ 25016-11-9 ]
  • [ 17647-70-0 ]
  • [ 167408-67-5 ]
  • C15H15N5O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methylpyrazole-4-carbaldehyde; 3-amino-4-methylfurazan; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 57
  • [ 25016-11-9 ]
  • [ 17647-70-0 ]
  • [ 20577-64-4 ]
  • C15H17N5O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methylpyrazole-4-carbaldehyde; 3-amino-4-methylfurazan; methyl 5-methyl-2,4-dioxohexanoate With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 58
  • [ 17647-70-0 ]
  • [ 20577-64-4 ]
  • [ 27258-33-9 ]
  • C15H17N5O4 [ No CAS ]
  • 59
  • [ 17647-70-0 ]
  • [ 1410097-04-9 ]
  • [ 27258-33-9 ]
  • C22H18N6O4 [ No CAS ]
  • 60
  • [ 17647-70-0 ]
  • [ 451485-68-0 ]
  • [ 619-66-9 ]
  • C21H14ClN3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-amino-4-methylfurazan; C11H9ClO4; 4-Carboxybenzaldehyde With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 61
  • [ 17647-70-0 ]
  • [ 100-52-7 ]
  • [ 20577-73-5 ]
  • C20H15N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-amino-4-methylfurazan; benzaldehyde; methyl 4-phenyl-2,4-dioxobutanoate With chloro-trimethyl-silane In N,N-dimethyl-formamide Sealed tube; Heating; Stage #2: With water In N,N-dimethyl-formamide at 20℃; for 2h; Sonication;
  • 62
  • [ 17647-70-0 ]
  • [ 104-88-1 ]
  • [ 20577-73-5 ]
  • C20H14ClN3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-amino-4-methylfurazan; 4-chlorobenzaldehyde; methyl 4-phenyl-2,4-dioxobutanoate With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 63
  • [ 17647-70-0 ]
  • [ 123-11-5 ]
  • [ 20577-73-5 ]
  • C21H17N3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-amino-4-methylfurazan; 4-methoxy-benzaldehyde; methyl 4-phenyl-2,4-dioxobutanoate With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 64
  • [ 17647-70-0 ]
  • [ 308115-74-4 ]
  • [ 1400399-52-1 ]
YieldReaction ConditionsOperation in experiment
18% Stage #1: 3-amino-4-methylfurazan With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: C9H6Cl2O3S In tetrahydrofuran at -78 - 20℃; for 18h; 1.2 To a solution of 4-methyl-1 ,2,5-oxadiazol-3-amine 3 (200 mg, 2.0 mmol) in THF (70 mL) was added LiHMDS (1.0 M solution in THF, 2.2 m L, 2.2 mmol) at -78 °C under a nitrogen atmosphere. The mixture was allowed to stir at -78 °C for 1 hour followed by the addition of a solution of acid chloride 2 (535 mg, 2.0 mmol) in THF (10 ml_). The reaction was allowed to warm to ambient temperature and stirred for 18 hours. The reaction mixture was quenched by slow addition of saturated aqueous NH4CI (40 ml_) and the aqueous layer was extracted with EtOAc (3 x 50 ml_). The combined organic layers were washed with saturated brine (30 ml_), dried (MgSO4) and concentrated. Purification of the obtained residue by preparative HPLC afforded the desired product A-1 of table 1 (120 mg, 18%). H NMR (CDCIs 400MHz): δ 7.97-7.85 (m, 2H), 7.79 (d, 1 H), 4.19 (s, 3H), 3.63-3.58 (m, 2H), 3.48-3.42 (m, 2H). Preparative HPLC purification:Column: Nucleodur C18 Gravity 5μηη (Macherey-Nagel GmbH & Co. KG, Germany); Column diameter: 50*100 mm;Mobile phase: acetonitrile + 0.05% trifluoroacetic acid (TFA)/water + 0.05% TFA, using a gradient from 25:75 to 70:30 over 7.5 minutes at 25°C, flow rate 128 ml/min.
  • 65
  • [ 17647-70-0 ]
  • [ 1435476-01-9 ]
  • [ 1435475-86-7 ]
YieldReaction ConditionsOperation in experiment
11.8% With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 22℃; for 16.5h; Inert atmosphere; 2.8 Example 2: Preparation of 2,4,6-trichloro-A/-(4-methyl-1 ,2,5-oxadiazol-3-yl)-3-(2,2,2- trifluoroethoxymethyl)benzamide (Compound A-82, Table 1 , hereinafter ?.?-82). Step 8)To a solution of compound 3 (0.3 g, 2.44 mmol) and the above prepared compound 8 in anhydrous THF (20 mL) was added LiHMDS (2.44 mL, 2.44 mmol) at -78 °C under N2. The mixture was stirred between -78 and -20 °C for 0.5 h. Further LiHMDS (4.88 mL, 4.88 mmol) was added at -20 °C and the mixture was allowed to warm to 22°C and stirred 16 h. The reaction was quenched with water and extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSC ) and concentrated in vacuo to afford the crude product, which was washed with CH2CI2 to afford the desired product ?.?-82 (120 mg, 1 1 .8 %). 1H NMR (CDCI3 400MHz): ? 7.99 (s, 1 H), 4.91 (s, 2H), 4.24 (q, 2H, J=9.2 Hz), 2.40 (s, 3H).
  • 66
  • [ 17647-70-0 ]
  • [ 4136-95-2 ]
  • [ 1435475-85-6 ]
YieldReaction ConditionsOperation in experiment
32.8% Stage #1: 3-amino-4-methylfurazan; 2,4,6-trichlorobenzoyl chloride With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 22℃; for 18h; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water 1.2 Example 1 : Preparation of 2,4,6-trichloro-A/-(4-methyl-1 ,2,5-oxadiazol-3-yl)benzamide (Compound A-2 of Table 1 , hereinafter ?.?-2). Step 2)2 3 A-2To a solution of compound 3 (0.25 g, 2 mmol) and the above prepared, crude compound 2 in anhydrous THF (20 mL) was added LiHMDS (2 mL, 2 mmol) at -78 °C under N2. The mixture was stirred between -78 °C and 22°C for 2 h. Further LiHMDS (4 mL, 4 mmol) was added at 0 °C and the mixture was allowed to warm to 22°C and stirred for 16 h. The reaction was quenched by addition of saturated aqueous NaHC03 and extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSC ) and concentrated under reduced pressure. Flash chromatography using petrol ether (boiling range 60-90°C) and EtOAc and further washing of the concentrated product with CH2CI2 afforded 1-A-2 (200 mg, 32.8 %). 1H NMR (CDCI3 400MHz): ? 1 1.78 (br. s, 1 H), 7.89 (s, 2H), 2.41 (s, 3H).
  • 67
  • [ 17647-70-0 ]
  • [ 82671-06-5 ]
  • [ 1399057-74-9 ]
YieldReaction ConditionsOperation in experiment
49% With dmap; triethylamine; In tetrahydrofuran; ethyl acetate; at 20℃; for 18h; Example 1 : 2,6-dichloro-5-fluoro-N-(4-methyl-1 ,2,5-oxadiazol-3-yl)pyridine-3- carboxamide (see compound of formula 1.2 of Table 12, where where R, R3, R4 and R5 correspond to line A-16 of table A = compound 1.2-16).To a solution of carboxylic acid 1 (635 mg, 3.0 mmol) and 4-methyl-1 ,2,5-oxadiazol-3- amine 2 (300 mg, 3.0 mmol) in THF (80 mL) were added sequentially Et3N (0.44 mL, 3.0 mmol), DMAP (74 mg, 0.6 mmol) and polyphosphonic anhydride (? 50 wt. % in EtOAc, 1 .55 mL, 3.0 mmol) at ambient temperature. The reaction was allowed to stir for 18 hours, then concentrated under reduced pressure. Water was added (200 ml) and the crude mixture allowed to stand for 3 days. The water was then decanted off and the residue taken up in CH2CI2, dried (MgS04) and concentrated to afford 2,6- dichloro-5-fluoro-N-(4-methyl-1 ,2,5-oxadiazol-3-yl)pyridine-3-carboxamide (430 mg, 49%). 1H NMR (CDCIs 400MHz): ? 8.91 (br. s, 1 H), 8.14 (d, 1 H), 2.47 (s, 3H).
  • 68
  • [ 17647-70-0 ]
  • [ 903522-29-2 ]
  • 3,5-difluoro-N-(4-methyl-1,2,5-oxadiazol-3-yl)isonicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% With dmap; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In tetrahydrofuran; dichloromethane; at 20℃; for 20h; Synthesis of 3,5-difluoro-N-(4-methyl-1,2,5-oxadiazol-3-yhisonicotinamide (Table example No. 2-6) [0084] 200 mg (1.26 mmol) of <strong>[903522-29-2]3,5-difluoroisonicotinic acid</strong> and 125 mg (1.26 mmol) of 4-methyl-1,2,5-oxadiazol-3-amine are dissolved at RT in 6 ml of dichloromethane, and 0.88 ml (6.29 mmol) of triethylamine, 31 mg (0.25 mmol) of DMAP and 1.20 g (1.89 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF) are added. The reaction mixture is stirred at RT for 20 h and then washed twice with 5 ml each time of water. The organic phase is dried over Na2SO4 and concentrated. The residue is purified by column chromatography (silica gel, heptane/ethyl acetate). Yield: 100 mg (31%).
  • 69
  • [ 17647-70-0 ]
  • [ 1198475-43-2 ]
  • [ 1399062-75-9 ]
YieldReaction ConditionsOperation in experiment
61% With dmap; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In tetrahydrofuran; dichloromethane at 20℃; for 20h; 3-41 Synthesis of 5-chloro-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(trifluoromethyl)pyridine-2-carboxamide (Table example No. 3-41) Synthesis of 5-chloro-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(trifluoromethyl)pyridine-2-carboxamide (Table example No. 3-41) [0085] 300 mg (1.33 mmol) of 5-chloro-3-(trifluoromethyl)pyridine-2-carboxylic acid and 132 mg (1.33 mmol) of 4-methyl-1,2,5-oxadiazol-3-amine are dissolved at RT in 10 ml of CH2Cl2, and 0.19 ml (1.33 mmol) of triethylamine, 32 mg (0.27 mmol) of DMAP and 1.27 g (2.00 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF) are added. The reaction mixture is stirred at RT for 20 h and then washed twice with 10 ml each time of water. The organic phase is dried over Na2SO4 and concentrated. The residue is purified by column chromatography (silica gel, heptane/ethyl acetate). Yield: 250 mg (61%).
  • 70
  • [ 17647-70-0 ]
  • [ 280566-45-2 ]
  • [ 1399056-22-4 ]
YieldReaction ConditionsOperation in experiment
16% With triethylamine; In tetrahydrofuran; dichloromethane; at 20℃; for 14h; A. CHEMICAL EXAMPLES Synthesis of 2-chloro-N-(1,2,5-oxadiazol-3-yl)-6-(trifluoromethypnicotinamide (Table example No. 1-3) 239 mg (1.06 mmol) of <strong>[280566-45-2]2-chloro-6-(trifluoromethyl)nicotinic acid</strong> and 1.6 g (2.0 mmol) of Mukaiyama reagent on polymer (1.25 mmol/g) are admixed with 15 ml of dichloromethane (abs.) and 0.31 g (3.03 mmol) of triethylamine. Then 100 mg (1.01 mmol) of 4-methyl-1,2,5-oxadiazol-3-ylamine are added. The reaction mixture is stirred at room temperature (RT) for 14 h. Subsequently, the solid is removed by means of a frit and washed with 10 ml of dichloromethane. The filtrate is concentrated and purified by chromatography using a silica gel column with heptane/ethyl acetate. Yield: 52 mg (16%).
  • 71
  • [ 17647-70-0 ]
  • [ 220696-97-9 ]
  • [ 1379659-18-3 ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate In acetonitrile at 80℃; for 4h; Reflux; Inert atmosphere; chemoselective reaction;
  • 72
  • [ 17647-70-0 ]
  • [ 1396456-75-9 ]
  • [ 68957-94-8 ]
  • [ 1400399-86-1 ]
YieldReaction ConditionsOperation in experiment
63% With hydrogenchloride; dmap; triethylamine; In tetrahydrofuran; n-heptane; dichloromethane; 1. Synthesis of 4-chloro-3-methoxy-N-(4-methyl-1,2,5-oxadiazol-3-yl)-2,3-dihydro-1-benzothiophene-5-carboxamide 1,1-dioxide (table example No. 1928) 1.00 g (3.14 mmol) of 4-chloro-3-methoxy-2,3-dihydro-1-benzothiophene-5-carboxylic acid 1,1-dioxide and 0.33 g (3.15 mmol) of 4-methyl-1,2,5-oxadiazol-3-yl-amine were dissolved at room temperature (RT) in 35 ml of CH2Cl2, 3.02 g (4.74 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF) were added and the mixture was stirred at RT for 1 h. Subsequently, 2.18 ml (15.64 mmol) of triethylamine and 75 mg (0.61 mmol) of 4-dimethylaminopyridine (DMAP) were added and the whole mixture was stirred at RT for 16 h. This was followed by washing with water and twice with 6N hydrochloric acid, drying of the organic phase over Na2SO4 and filtration with suction through silica gel, washing through with 1:2 heptane/ethyl acetate and concentration. Yield 708 mg (63%). 1H NMR (CDCl3): delta=2.44 (s, 3H), 3.53 (s, 3H), 3.57 (dd, 1H), 3.71 (d, 1H), 5.15 (d, 1H), 7.55 (d, 1H), 7.74 (d, 1H), 9.40 (s, 1H)
  • 73
  • [ 17647-70-0 ]
  • [ 30169-25-6 ]
  • [ 1379659-10-5 ]
  • 74
  • [ 17647-70-0 ]
  • 2,4-dichloro-3-[(cyclopropylmethoxy)imino]methyl}benzoic acid [ No CAS ]
  • 2,4-dichloro-3-{(E)-[(cyclopropylmethoxy)imino]methyl}-N-(4-methyl-1,2,5-oxadiazol-3-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: 3-amino-4-methylfurazan; 2,4-dichloro-3-[(cyclopropylmethoxy)imino]methyl}benzoic acid With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane at 10 - 20℃; for 1h; Stage #2: With dmap; triethylamine In dichloromethane at 20℃; for 48h; A.4 4. Synthesis of 2,4-dichloro-3-{(E)-[(cyclopropylmethoxy)imino]methyl}-N-(4-methyl-1,2,5-oxadiazol-3-yl)benzamide (Table example 3-004) 4. Synthesis of 2,4-dichloro-3-{(E)-[(cyclopropylmethoxy)imino]methyl}-N-(4-methyl-1,2,5-oxadiazol-3-yl)benzamide (Table example 3-004) 400 mg (1.39 mmol) of 2,4-dichloro-3-[(cyclopropylmethoxy)imino]methyl}benzoic acid and 14418 mg (1.39 mmol) of 4-methyl-1,2,5-oxadiazole-3-amine were dissolved in 10 ml of CH2Cl2, 1.33 g (2.08 mmol) of propanephosphonic anhydride were added at 10-20° C. and the mixture was stirred at RT for 1 h. 700 mg of triethylamine and 34.6 mg (0.278 mmol) of DMAP were then added, and the mixture was stirred at RT for 2 days. The mixture was washed with water and twice with 6N hydrochloric acid and the organic phase was then dried over MgSO4 and concentrated. The residue was purified chromatographically on a silica gel column (heptane/ethyl acetate 4:1). Yield: 248.6 mg (48%) as a colorless solid. 1H-NMR (400 MHz, CDCl3 δ, ppm) 8.30 (s, 1H), 8.19 (br, s, 1H), 7.66 (d, 1H), 7.51 (d, 1H), 4.06 (d, 2H), 2.49 (s, 3H), 1.25 (m, 1H), 0.61 (m, 2H), 0.37 (m, 2H).
  • 75
  • [ 17647-70-0 ]
  • 2,4-dichloro-3-[(4-oxido-1,4-λ4-oxathian-4-ylidene)amino]benzoic acid [ No CAS ]
  • 2,4-dichloro-3-[(4-oxido-1,4-λ4-oxathian-4-ylidene)amino]-N-(4-methyl-1,2,5-oxadiazol-3-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90 mg Stage #1: 3-amino-4-methylfurazan; 2,4-dichloro-3-[(4-oxido-1,4-λ4-oxathian-4-ylidene)amino]benzoic acid With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In tetrahydrofuran; dichloromethane at 20℃; for 1h; Stage #2: With dmap; triethylamine In tetrahydrofuran; dichloromethane at 20℃; for 72h; 3 Step 3: Syntheses of 2,4-dichloro-3-[(4-oxido-1,4-λ4-oxathian-4-ylidene)amino]-N-(4-methyl-1,2,5-oxadiazol-3-yl)benzamide 200 mg (0.62 mmol) of 2,4-dichloro-3-[(4-oxido-1,4-λ4-oxathian-4-ylidene)amino]benzoic acid and 67.2 mg (0.68 mmol) of 4-methyl-1,2,5-oxadiazol-3-yl-amine in 15 ml of CH2Cl2 were admixed with 589 mg (0.93 mmol; 50% solution in THF) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide. The mixture was stirred at RT for 1 h. Subsequently, 312 mg (3.09 mmol) of NEt3 were added dropwise, then a catalytic amount of 4-(dimethylamino)pyridine. The contents were stirred at RT for three days. For workup, the mixture was washed with 1M hydrochloric acid. After the phase separation, the contents were concentrated and the residue was purified by chromatography, which gave 90 mg of clean product.
  • 76
  • [ 17647-70-0 ]
  • 4,4'-dimethylazofurazan [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With nickel(II) sulphate; sodium acetate; sodium hydroxide In water at 25℃; Electrolysis;
With perchloric anhydride In tetrachloromethane at 0℃;
  • 77
  • [ 17647-70-0 ]
  • 3-isopropyl-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylic acid [ No CAS ]
  • 3-isopropyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
168 mg Stage #1: 3-isopropyl-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 0.333333h; Stage #2: 3-amino-4-methyl-1,2,5-oxadiazole With triethylamine In dichloromethane at 20℃; for 1h; 5 3-Isopropyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4, 3-a]pyridine-8-carboxamide (Compound No. 3-001) Synthesis Example 5 3-Isopropyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4, 3-a]pyridine-8-carboxamide (Compound No. 3-001) To the mixed solution of 165 mg (0.60 mmol) of 3-isopropyl-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylic acid, 0.1 ml of N,N-dimethylformamide, and 5 ml of methylene chloride, 83 mg (0.66 mmol) of oxalyl chloride was added at room temperature. After completion of the addition, the reaction mixture was stirred for 20 minutes at room temperature. After completion of stirring, the mixed solution of 119 mg (1.21 mmol) of 4-methyl-1,2,5-oxadiazol-3-amine, 122 mg (1.21 mmol) of triethylamine, and 3 ml of methylene chloride was added. After completion of the addition, the reaction mixture was stirred for 1 hour at room temperature. After completion of stirring, the solvent was distilled away under reduced pressure. The obtained residue was purified with silica gel chromatography (n-hexane:ethyl acetate=9:1 to 2:1) to give 168 mg of the target product as a white solid. Melting point: 185° C. to 186° C.
168 mg Stage #1: 3-isopropyl-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 3-amino-4-methyl-1,2,5-oxadiazole With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; 5 synthesis of 3-isopropyl-N- (4-methyl-1,2,5-oxadiazol-3-yl) -5- (trifluoromethyl) - [1,2,4] triazolo [4,3- a] pyridine -8-carboxamide 165 mg (0.60 mmol) of 3-isopropyl-5- (trifluoromethyl) - [1,2,4] triazolo [4,3- a] pyridine-8-carboxylic acid, 0.1 ml of N, N-dimethylformamide and 83 mg (0.66 mmol) of oxalyl chloride was added to a mixed solution of 5 ml of methylene chloride at room temperature. After the addition was completed, the reaction mixture was stirred at room temperature for 20 minutes. After completion of stirring, a mixed solution of 119 mg (1.21 mmol) of 4-methyl-1,2,5-oxadiazol-3-amine, 122 mg (1.21 mmol) of triethylamine and 3 ml of methylene chloride was added. After completion of the addition, the reaction mixture was stirred at room temperature for 1 hour. After completion of stirring, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane: ethyl acetate = 9: 1 to 2: 1) to obtain 168 mg of the objective compound as a white solid.
168 mg Stage #1: 3-isopropyl-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 0.333333h; Stage #2: 3-amino-4-methyl-1,2,5-oxadiazole With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; 5 3-isopropyl-N- (4-methyl-1,2,5-oxadiazol-3-yl) -5- (trifluoromethyl) - [1,2,4] triazolo [4,3- a] pyridine -8-carboxamide(Compound No. 3-001) 165 mg (0.60 mmol) of 3-isopropyl-5- (trifluoromethyl) - [1,2,4] triazolo [4,3- a] pyridine-8-carboxylic acid, 0.1 ml of N, N-dimethylformamide and 83 mg (0.66 mmol) of oxalyl chloride was added to a mixed solution of 5 ml of methylene chloride at room temperature. After completion of the addition, the reaction mixture was stirred at room temperature for 20 minutesFollowed by stirring.After completion of the stirring, a mixed solution of 119 mg (1.21 mmol) of 4-methyl-1,2,5-oxadiazol-3-amine, 122 mg (1.21 mmol) of triethylamine and 3 ml of methylene chloride was added. After completion of the addition, the reaction mixture was stirred at room temperature for 1 hour. After stirring was completed, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane: ethyl acetate = 9: 1 to 2: 1) to obtain 168 mg of the objective compound as a white solid.
168 mg Stage #1: 3-isopropyl-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 3-amino-4-methyl-1,2,5-oxadiazole With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; 5 3-Isopropyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide (Compound No. 3-001) In a mixed solution of 3-isopropyl-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-8-carboxylic acid 165 mg (0.60 mmol), N,N-dimethylformamide 0.1 ml and 5 ml of methylene chloride,At room temperature, 83 mg (0.66 mmol) of oxalyl chloride was added.After completion of the addition, the reaction mixture was stirred at room temperature for 20 minutes.After completion of stirring, a mixed solution of 4-methyl-1,2,5-oxadiazole-3-amine 119 mg (1.21 mmol), triethylamine 122 mg (1.21 mmol) and methylene chloride 3 ml was added.After completion of the addition, the reaction mixture was stirred at room temperature for 1 hour. After the stirring was completed, the solvent was distilled off under reduced pressure.The obtained residue was purified by silica gel chromatography (n-hexane: ethyl acetate = 9: 1 to 2: 1) to obtain 168 mg of the target product as a white solid.
168 mg Stage #1: 3-isopropyl-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 3-amino-4-methyl-1,2,5-oxadiazole With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; 5 [Synthesis Example 5] 3-Isopropyl-N- (4-methyl-1,2,5-oxadiazole-3-yl) -5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine -8-Carboxamide (Compound No. 3-001) 3-Isopropyl-5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine-8-carboxylic acid 165 mg (0.60 mmol), N, N-dimethylformamide 0.1 ml and 83 mg (0.66 mmol) of oxalyl chloride was added to a mixed solution of 5 ml of methylene chloride at room temperature. After completion of the addition, the reaction mixture was stirred at room temperature for 20 minutes. After completion of stirring, a mixed solution of 4-methyl-1,2,5-oxadiazole-3-amine 119 mg (1.21 mmol), triethylamine 122 mg (1.21 mmol) and methylene chloride 3 ml was added. After completion of the addition, the reaction mixture was stirred at room temperature for 1 hour. After the stirring was completed, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane: ethyl acetate = 9: 1 to 2: 1) to obtain 168 mg of the target product as a white solid.

  • 78
  • [ 17647-70-0 ]
  • C11H9ClF3N3O [ No CAS ]
  • 3-isopropyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4, 3-a]pyridine-8-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
168 mg With triethylamine In dichloromethane at 20℃; for 1h; 5.1 3-isopropyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide (compound No.3-001) 3-isopropyl-5- (trifluoromethyl) - [l, 2,4] triazolo [4,3-a] pyridine-8-carboxylic acid 165mg (0.60mmol), N, N- dimethylformamide 0.1 ml and the mixture of 5ml of methylene chloride, was added oxalyl chloride 83mg (0.66mmol) at room temperature. After the addition was completed, the reaction mixture was stirred at room temperature for 20 minutes. After completion of the stirring, 4-methyl -1,2,5- oxadiazol-3-amine119mg (1.21mmol), it was added triethylamine and 122mg (1.21mmol) and a mixture of methylene chloride 3ml. After the addition was completed, the mixture was stirred for 1 hour at room temperature the reaction mixture. After completion of the stirring, and distilling off the solvent under reduced pressure. The obtained residue was purified by silica gel chromatography (n- hexane: ethyl acetate = 9: 1 ~ 2: 1) to give the desired product as a white solid, 168mg.
  • 79
  • [ 17647-70-0 ]
  • 2-methyl-3-methylsulfanyl-4-(trifluoromethyl)benzaldehyde [ No CAS ]
  • 1-[2-methyl-3-methylsulfanyl-4-(trifluoromethyl)phenyl]-N-(4-methyl-1,2,5-oxadiazol-3-yl)methanimine [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% In toluene at 110℃; for 96h; Molecular sieve; 4 1-[2-Methyl-3-methylsulfanyl-4-(trifluoromethyl)phenyl]-N-(4-methyl-1,2,5-oxadiazol-3-yl)methanimine 46 A solution of 2-methyl-3-methylsulfanyl-4-(trifluoromethyl)benzaldehyde 45 (184 mg, 0.788 mmol) and 4-methyl-1,2,5-oxadiazol-3-amine (78 mg, 0.788 mmol) in toluene (3 mL) was heated at 110° C. over 4 molecular sieves and MgSO4 for 96 h after which time the mixture was filtered and concentrated to give the title compound as a colourless solid (176 mg, 71%). (0344) 1H NMR δH (300 MHz, CDCl3); 9.31 (s, 1H), 8.16 (d, J=8.0 Hz, 1H), 7.63 (d, J=8.0 Hz, 1H), 2.88 (s, 3H), 2.37 (s, 3H), 2.22 (s, 3H); EI-MS 315 [M+].
  • 80
  • [ 17647-70-0 ]
  • C10H8ClF3OS [ No CAS ]
  • [ 1279112-00-3 ]
YieldReaction ConditionsOperation in experiment
32% Stage #1: 3-amino-4-methylfurazan With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Stage #2: C10H8ClF3OS In tetrahydrofuran at -30 - 20℃; for 16h; 4 2-Methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-methylsulfanyl-4-(trifluoromethyl)benzamide 48 Oxalyl chloride (120 μL, 1.20 mmol) was added to a solution of 2-methyl-3-methylsulfanyl-4-(trifluoromethyl)benzoic acid (200 mg, 0.80 mmol) and N,N-dimethylformamide (2 drops) in dichloromethane (3.5 mL) and the mixture was stirred at room temperature for 2 h. (0350) Concentration under reduced pressure gave the crude acid chloride (0.80 mmol), which was used without further purification. (0351) Sodium bis(trimethylsilyl)amide (1M solution in tetrahydrofuran, 1.2 mL, 1.20 mmol) was added to a solution of 4-methyl-1,2,5-oxadiazol-3-amine (95 mg, 96 mmol) in tetrahydrofuran (2 mL) at -78° C. and the mixture was stirred at that temperature for 1 h. The mixture was gradually allowed to warm to -30° C. and a solution of the acid chloride (0.8 mmol) in tetrahydrofuran (2 mL) was added. The mixture was allowed to warm to room temperature and was stirred for 16 h. Saturated ammonium chloride solution (10 mL) and ethyl acetate (10 mL) were added, the organic layer separated and the aqueous layer further extracted with ethyl acetate (2×15 mL). The combined organic phases were dried (MgSO4), filtered and concentrated to give the crude product which was purified by flash chromatography on silica gel (solvent 33% Et2O/hexane) to afford the title compound as a colourless oil (84 mg, 32%). (0352) 1H NMR δH (300 MHz, CDCl3); 7.78 (br s, 1H), 7.56 (d, J=8.0 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H), 2.65 (s, 3H), 2.35 (s, 3H), 2.16 (s, 3H); ESI-MS 354.0 [MNa+]. (0353) Compound 48 forms part of the prior art (WO2011/035874) and is included for reference purposes only.
  • 81
  • [ 17647-70-0 ]
  • (E)-3,4-di-O-acetylcaffeoyl chloride [ No CAS ]
  • (E)-4-(3-((4-methyl-1,2,5-oxadiazol-3-yl)amino)-3-oxoprop-1-en-1-yl)-1,2-phenylene diacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.200 g In dichloromethane Reflux; General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
  • 82
  • [ 141-97-9 ]
  • [ 17647-70-0 ]
YieldReaction ConditionsOperation in experiment
27% Stage #1: ethyl acetoacetate With sodium hydroxide In water at 10 - 20℃; Stage #2: With perchloric acid; sodium nitrite at 10 - 20℃; Further stages;
  • 83
  • [ 17647-70-0 ]
  • [ 598-21-0 ]
  • 2-bromo-N-(4-methyl-1,2,5-oxadiazol-3-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With N-ethyl-N,N-diisopropylamine In dichloromethane at -20 - 20℃; for 1h; 2-Bromo-N-(4-methyl-1,2,5-oxadiazol-3-yl)acetamide To a -20 C solution of 4-methyl-1,2,5-oxadiazol-3-amine (0.500 g, 5.05 mmol) and distilled diisopropylethylamine (0.970 mL, 5.55 mmol) in dry dichloromethane (25 mL), bromoacetyl bromide (1.25 mL, 5.55 mmol) was added dropwise with stirring. The reaction stirred at -20 C for 20 minutes then slowly warmed to room temperature over 10 minutes and stirred for an additional 30 minutes. The reaction mixture was diluted with water (10 mL) then stirred for a further 30 minutes. The organic layer was separated and washed with water (3 x 10 mL), dried with magnesium sulfate and concentrated in vacuo. The crude product was subjected to column chromatography (silica; 15:75 ethyl acetate/hexanes elution) to afford compound 2 (0.677 g, 61%), mp 120-128 C. 1H NMR (400 MHz, CDCl3): δ 8.37 (s, 1H), 4.08 (s, 2H), 2.42 (s, 3H). 13C NMR (100 MHz, CDCl3): δ 164.4, 149.8, 148.0, 27.8, 9.2. LRMS (ESI): m/z 242.5 (M+Na)+.
  • 84
  • [ 17647-70-0 ]
  • [ 102-92-1 ]
  • N-(4-methyl-1,2,5-oxadiazol-3-yl)cinnamamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
5% With sodium hydrogencarbonate In tetrahydrofuran at 0 - 20℃; Inert atmosphere; N-(4-Methyl-1,2,5-oxadiazol-3-yl)cinnamamide To a solution of 4-methyl-1,2,5-oxadiazol-3-amine (0.200 g, 2.02 mmol) in dry tetrahydrofuran (7.90 mL) cooled to 0 °C under nitrogen, cinnamoyl chloride (0.404 g, 2.42 mmol) in dry tetrahydrofuran (2 mL) was added dropwise with stirring. Sodium bicarbonate (0.176 g, 2.09 mmol) was then added and the resulting mixture stirred at room temperature overnight. The reaction was quenched with water (9 mL) then extracted with ethyl acetate (3 x 10 mL). The organic layer was dried with magnesium sulfate and the solution concentrated by rotary evaporation. The crude product was purified by column chromatography (silica; 10:90 ethyl acetate/hexanes elution). The product was eluted with residual cinnamic acid so it was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution (1 x 15 mL) to yield compound 18 (22.0 mg, 5%), mp 130-137 °C. 1H NMR (400 MHz, CDCl3): δ 7.83 (d, J = 15.6, 1H), 7.56 (s, 1H), 7.58 (dd, J = 6.0, 2.4, 2H), 7.44-7.42 (m, 3H), 6.65 (d, J = 14.4, 1H), 2.48 (s, 3H). 13C NMR (100 MHz, DMSO): 163.9, 151.0, 148.4, 142.7, 134.2, 130.4, 129.1, 128.1, 119.7, 8.7. LRMS (ESI): m/z 230.0 (M+H)+. HRMS (ESI): (M+H)+ calcd for C12H12N3O2+, 230.0929; found, 230.0929.
  • 85
  • [ 17647-70-0 ]
  • [ 701-99-5 ]
  • N-(4-methyl-1,2,5-oxadiazol-3-yl)-2-phenoxyacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.103 g In dichloromethane for 2h; Reflux; N-(4-Methyl-1,2,5-oxadiazol-3-yl)-2-phenoxyacetamide To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%), mp 132-134 °C. 1H NMR (500 MHz, CDCl3): δ 8.61 (s, 1H), 7.37 (t, J = 8.25, 2H), 7.10 (t, J = 6.5, 1H), 6.98 (dd, J = 9.0, 1.0, 2H), 4.70 (s, 2H), 2.45 (s, 3H). 13C NMR (125 MHz, CDCl3): δ 167.1, 156.7, 149.8, 148.1, 130.2, 123.1, 114.9, 67.3, 9.53. LRMS (ESI): m/z 256.0 (M+Na)+. HRMS (ESI): (M+H)+ calcd for C11H12N3O3+, 234.0878; found, 234.0878.
  • 86
  • [ 17647-70-0 ]
  • [ 7031-27-8 ]
  • N-(4-methyl-1,2,5-oxadiazol-3-yl)-2-(phenylthio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
243 g In dichloromethane Reflux; General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
  • 87
  • [ 17647-70-0 ]
  • [ 20143-41-3 ]
  • 2-(2-chlorophenoxy)-N-(4-methyl-1,2,3-oxadiazol-3-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
177 mg In dichloromethane Reflux; General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
  • 88
  • [ 17647-70-0 ]
  • [ 4122-68-3 ]
  • 2-(4-chlorophenoxy)-N-(4-methyl-1,2,5-oxadiazol-3-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.153 g In dichloromethane Reflux; General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
  • 89
  • [ 17647-70-0 ]
  • [ 85630-84-8 ]
  • 2-(2,3-dichlorophenoxy)-N-(4-methyl-1,2,5-oxadiazol-3-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.179 g In dichloromethane Reflux; General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
  • 90
  • [ 17647-70-0 ]
  • [ 20143-45-7 ]
  • 2-(3,4-dichlorophenoxy)-N-(4-methyl-1,2,5-oxadiazol-3-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.207 g In dichloromethane Reflux; General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
  • 91
  • [ 17647-70-0 ]
  • [ 2007-12-7 ]
  • N-(4-methyl-1,2,5-oxadiazol-3-yl)-2-(naphthalene-1-yloxy)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.042 g In dichloromethane Reflux; General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
  • 92
  • [ 17647-70-0 ]
  • [ 879-18-5 ]
  • N-(4-methyl-1,2,5-oxadiazol-3-yl)-1-naphthamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.203 g In dichloromethane Reflux; General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
  • 93
  • [ 17647-70-0 ]
  • [ 2243-83-6 ]
  • N-(4-methyl-1,2,5-oxadiazol-3-yl)-2-naphthamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.111 g In dichloromethane Reflux; General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
  • 94
  • [ 17647-70-0 ]
  • [ 645-45-4 ]
  • N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
165 mg In dichloromethane Reflux; General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
  • 95
  • [ 17647-70-0 ]
  • [ 15893-42-2 ]
  • 3-(4-methoxyphenyl)-N-(4-methyl-1,2,5-oxadiazol-3-yl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.284 g In dichloromethane Reflux; General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
  • 96
  • [ 17647-70-0 ]
  • [ 20996-40-1 ]
  • (E)-2-(3-((4-methyl-1,2,5-oxadiazol-3-yl)amino)-3-oxoprop-1-en-1-yl)phenyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.094 g In dichloromethane Reflux; General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
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[ 17647-70-0 ]

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[ 17647-70-0 ]

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