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[ CAS No. 153493-48-2 ] {[proInfo.proName]}

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Chemical Structure| 153493-48-2
Chemical Structure| 153493-48-2
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Product Details of [ 153493-48-2 ]

CAS No. :153493-48-2 MDL No. :MFCD00187160
Formula : C4Cl2N4O Boiling Point : -
Linear Structure Formula :- InChI Key :VCQNGLLLIXRNIO-UHFFFAOYSA-N
M.W : 190.98 Pubchem ID :605330
Synonyms :

Calculated chemistry of [ 153493-48-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 37.41
TPSA : 64.7 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.67
Log Po/w (XLOGP3) : 1.63
Log Po/w (WLOGP) : 1.32
Log Po/w (MLOGP) : 0.64
Log Po/w (SILICOS-IT) : 2.02
Consensus Log Po/w : 1.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.66
Solubility : 0.421 mg/ml ; 0.00221 mol/l
Class : Soluble
Log S (Ali) : -2.6
Solubility : 0.478 mg/ml ; 0.0025 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.03
Solubility : 0.177 mg/ml ; 0.000929 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.57

Safety of [ 153493-48-2 ]

Signal Word:Warning Class:
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 153493-48-2 ]

* 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 [ 153493-48-2 ]

[ 153493-48-2 ] Synthesis Path-Downstream   1~85

  • 3
  • [ 153493-48-2 ]
  • 4H,7H-[1,2,5]Oxadiazolo[3,4-b]pyrazine-5,6-dione dioxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With sodium hydroxide; hydroxylamine hydrochloride In diethyl ether; water for 13h; Ambient temperature;
93% With hydroxylamine hydrochloride; sodium hydroxide In diethyl ether; water at 20℃; 4 Example 4. Synthesis of Compound 5 In an ice bath, To a solution of hydroxylamine hydrochloride (34.7 g, 500 mmol) in water (90 mL) was added NaOH (20 g,A solution of 500 mmol of water (50 mL) was added followed by diethyl ether (25 mL).Compound 4 (24.4 g, 127.7 mmol) was then added, stirred for 1 h at room temperature, and the mixture was allowed to stand at room temperature overnight. The resulting solid was filtered, washed with water and acetone and dried to give compound 5 (22.0 g, 93%).
92% With hydroxylamine
  • 5
  • [ 4418-61-5 ]
  • [ 153493-48-2 ]
  • 9<i>H</i>-6-oxa-1,2,3,3a,4,5,7,8,9-nonaaza-cyclopenta[<i>a</i>]-<i>s</i>-indacene [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With triethylamine In acetonitrile at 20℃; for 1h;
  • 6
  • [ 2933-81-5 ]
  • [ 153493-48-2 ]
  • 8-(4-chloro-phenyl)-7,8-dihydro-6<i>H</i>-2,5-dioxa-1,3,4,8,9-pentaaza-cyclopenta[<i>b</i>]naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With triethylamine In acetonitrile at 20℃; for 1h;
  • 7
  • [ 100-02-7 ]
  • [ 153493-48-2 ]
  • 5,6-bis-(4-nitro-phenoxy)-[1,2,5]oxadiazolo[3,4-<i>b</i>]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With potassium hydroxide at 5 - 10℃; for 2h;
  • 8
  • [ 372-19-0 ]
  • [ 153493-48-2 ]
  • N5,N6-bis(3-fluorophenyl)[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With N,N-diethylaniline In acetonitrile Heating;
With N,N-diethylaniline In acetonitrile Reflux;
  • 9
  • [ 34801-09-7 ]
  • [ 153493-48-2 ]
  • <i>N</i>-{2-[6-(2-acetylamino-phenylamino)-[1,2,5]oxadiazolo[3,4-<i>b</i>]pyrazin-5-ylamino]-phenyl}-acetamide [ No CAS ]
  • 10
  • [ 64-17-5 ]
  • [ 153493-48-2 ]
  • 5,6-diethoxyfurazano[3,4-b]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With potassium hydroxide at 5 - 10℃; for 2h;
With potassium carbonate In acetonitrile
  • 14
  • [ 2986-19-8 ]
  • [ 153493-48-2 ]
  • 6-methylsulfanyl-5<i>H</i>-imidazo[4,5-<i>b</i>][1,2,5]oxadiazolo[3,4-<i>e</i>]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With triethylamine In acetonitrile at 20℃; for 1h;
  • 16
  • [ 106-47-8 ]
  • [ 153493-48-2 ]
  • (4-chlorophenyl){6-[(4-chlorophenyl)amino](1,2,5-oxadiazolo[3,4-e]pyrazin-5-yl)}amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With N,N-diethylaniline In acetonitrile Heating;
With N,N-diethylaniline In acetonitrile Reflux;
  • 17
  • [ 96-50-4 ]
  • [ 153493-48-2 ]
  • 6-oxa-1-thia-3a,4,5,7,8,9-hexaaza-cyclopenta[<i>a</i>]-<i>s</i>-indacene [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With triethylamine In acetonitrile at 20℃; for 1h;
  • 18
  • [ 75-04-7 ]
  • [ 153493-48-2 ]
  • <i>N</i>,<i>N</i>'-diethyl-[1,2,5]oxadiazolo[3,4-<i>b</i>]pyrazine-5,6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% In acetonitrile at 5 - 10℃; for 2h;
  • 19
  • [ 141-43-5 ]
  • [ 153493-48-2 ]
  • 7,8-dihydro-1,4-oxazino[2,3-e]furazano[3,4-b]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With triethylamine In acetonitrile at 20℃; for 1h;
  • 20
  • [ 108-98-5 ]
  • [ 153493-48-2 ]
  • 5,6-bis-phenylsulfanyl-[1,2,5]oxadiazolo[3,4-<i>b</i>]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With triethylamine In acetonitrile for 0.5h;
  • 22
  • [ 496-72-0 ]
  • [ 153493-48-2 ]
  • 7-methyl-5,10-dihydro-2-oxa-1,3,4,5,10,11-hexaaza-cyclopenta[<i>b</i>]anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With triethylamine In acetonitrile at 20℃; for 1h;
  • 23
  • [ 63-74-1 ]
  • [ 153493-48-2 ]
  • C16H14N8O5S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With N,N-diethylaniline In acetonitrile Heating;
  • 25
  • [ 109-73-9 ]
  • [ 153493-48-2 ]
  • <i>N</i>,<i>N</i>'-dibutyl-[1,2,5]oxadiazolo[3,4-<i>b</i>]pyrazine-5,6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% In acetonitrile at 5 - 10℃; for 2h;
With N,N-diethylaniline In acetonitrile Reflux;
  • 26
  • [ 62-53-3 ]
  • [ 153493-48-2 ]
  • N5,N6-diphenyl[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% In acetonitrile at 5 - 10℃; for 2h;
With N,N-diethylaniline In acetonitrile Reflux;
  • 27
  • [ 3179-31-5 ]
  • [ 153493-48-2 ]
  • 6-oxa-9-thia-1,2,3a,4,5,7,8-heptaaza-cyclopenta[<i>a</i>]-<i>s</i>-indacene [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With triethylamine In acetonitrile at 20℃; for 1h;
  • 28
  • [ 108-42-9 ]
  • [ 153493-48-2 ]
  • N,N'-bis-(3-chloro-phenyl)-[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With N,N-diethylaniline In acetonitrile Heating;
74% With N,N-diethylaniline In ethyl acetate at -60 - 20℃; 1 Example 1. BN,N'-Bis-(3-chloro-phenyl)-[l,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine; To a dry roundbottom flask was added A and ethyl acetate (80 ml). To this stirred solution under a nitrogen atmosphere at -600C was added dropwise a solution of B and N,N'-diethylaniline in ethyl acetate (20 ml). A purple solution was rapidly formed during addition. The cooling bath was removed and the reaction mixture was allowed to warm to RT overnight. The reaction mixture was partitioned against water, washed with brine and dried over MgSO4. The solvent was evaporated to dryness to give a solid. This solid was washed with hexanes to remove most of the impurities. An attempt to dissolve the solid in dichloromethane (200 ml) was made but an off-white solid didn't dissolve and was EPO filtered off. When the dichloromethane was reduced to 100 ml a second batch of off- white solids was filtered off. Finally the volume was reduced to 50 ml to give a third batch of off-white solids. All batches were pure according to IH-NMR. (NMR nr.: 9000013152094). The yield of the pure compound was 2469 mg (6.62 mmol, 74%). 1H NMR (DMSOd6) δ 10.07 (2H, s); 8.00 (2H, s); 7.78 (IH, d); 7.52 (2H, dd); 7.31 (2H, d); NMR ID-nr.: H_RR_2034416; Melting point: 237.8 - 238.5°C
  • 29
  • [ 95-54-5 ]
  • [ 153493-48-2 ]
  • 5,10-dihydro-2-oxa-1,3,4,5,10,11-hexaaza-cyclopenta[<i>b</i>]anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% In acetonitrile at 20℃; for 3h;
  • 30
  • [ 95-55-6 ]
  • [ 153493-48-2 ]
  • 10<i>H</i>-2,5-dioxa-1,3,4,10,11-pentaaza-cyclopenta[<i>b</i>]anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With triethylamine In acetonitrile at 20℃; for 1h;
  • 31
  • [ 137-07-5 ]
  • [ 153493-48-2 ]
  • 10<i>H</i>-2-oxa-5-thia-1,3,4,10,11-pentaaza-cyclopenta[<i>b</i>]anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With triethylamine In acetonitrile at 20℃; for 1h;
  • 32
  • [ 95-51-2 ]
  • [ 153493-48-2 ]
  • N5,N6-bis(2-chlorophenyl)[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With N,N-diethylaniline In acetonitrile Heating;
  • 33
  • [ 1455-77-2 ]
  • [ 153493-48-2 ]
  • 9<i>H</i>-6-oxa-1,2,3a,4,5,7,8,9-octaaza-cyclopenta[<i>a</i>]-<i>s</i>-indacen-3-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With triethylamine In acetonitrile at 20℃; for 1h;
  • 34
  • [ 153493-48-2 ]
  • C4H9N3S [ No CAS ]
  • (6-imino-2-oxa-5-thia-1,3,4,7,8-pentaaza-<i>s</i>-indacen-7-yl)-isopropylidene-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With triethylamine In acetonitrile at 20℃; for 1h;
  • 35
  • [ 153493-48-2 ]
  • 5-ethyl-3<i>H</i>-[1,3,4]thiadiazol-2-ylideneamine [ No CAS ]
  • 2-ethyl-6-oxa-1-thia-3,3a,4,5,7,8,9-heptaaza-cyclopenta[<i>a</i>]-<i>s</i>-indacene [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With triethylamine In acetonitrile at 20℃; for 1h;
  • 36
  • [ 153493-48-2 ]
  • [ 186205-15-2 ]
YieldReaction ConditionsOperation in experiment
58% With ammonium hydroxide In acetonitrile at 5 - 10℃; for 2h;
  • 37
  • [ 153493-48-2 ]
  • C4H4N6O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With hydroxylamine In acetonitrile at 5 - 10℃; for 2h;
  • 38
  • [ 153493-48-2 ]
  • [ 60-23-1 ]
  • 7,8-dihydro-6<i>H</i>-2-oxa-5-thia-1,3,4,8,9-pentaaza-cyclopenta[<i>b</i>]naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine In acetonitrile at 20℃; for 1h;
  • 40
  • [ 153493-48-2 ]
  • [ 99-09-2 ]
  • 5,6-di(3-nitroanilino)furazano[3,4-b]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With N,N-diethylaniline In acetonitrile Heating;
  • 41
  • [ 153493-48-2 ]
  • [ 74-89-5 ]
  • <i>N</i>,<i>N</i>'-dimethyl-[1,2,5]oxadiazolo[3,4-<i>b</i>]pyrazine-5,6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In acetonitrile at 5 - 10℃; for 2h;
  • 42
  • [ 153493-48-2 ]
  • [ 156-87-6 ]
  • 6,7,8,9-tetrahydro-2,5-dioxa-1,3,4,9,10-pentaaza-cyclohepta[<i>f</i>]indene [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With triethylamine In acetonitrile at 20℃; for 1h;
  • 43
  • [ 153493-48-2 ]
  • [ 95-53-4 ]
  • N5,N6-di-o-tolyl[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine In acetonitrile for 0.5h;
35% In tetrahydrofuran for 13h; Reflux; 1 Synthesis of Symmetrical Oxadiazolo-Pyrazine Diarylamine Compounds General procedure: Symmetric 5,6-Dichloro-[1,2,5]oxadiazolo[3,4-b]pyrazine (2, 1 equiv.) was dissolved in THF (0.6 M solution). The desired substituted arylamine (3 equiv.) was then added. The reaction mixture was allowed reflux for 13 h. After which, the solution was concentrated via vacuum, and the residue was purified by silica gel column chromatography to yield the title compound; Synthesized by general procedure A.35%, yellow solid.1H NMR (400 MHz, Acetone-d6) 9.36 (s, 2H), 7.58-7.52 (m, 2H), 7.40- 7.25 (m, 6H), 2.34 (s, 6H); HRMS (ESI+): Calcd for C18H17N6O+ [M+H]+: 333.1464, Found: 333.1470.
35% In tetrahydrofuran Reflux;
  • 44
  • [ 153493-48-2 ]
  • [ 371-40-4 ]
  • (4-fluorophenyl){6-[(4-fluorophenyl)amino](1,2,5-oxadiazolo[3,4-e]pyrazin-5-yl)}amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With N,N-diethylaniline In acetonitrile Heating;
With N,N-diethylaniline In acetonitrile Reflux;
  • 45
  • [ 153493-48-2 ]
  • [ 60-24-2 ]
  • 6,7-dihydro-2,5-dioxa-8-thia-1,3,4,9-tetraaza-cyclopenta[<i>b</i>]naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine In acetonitrile at 20℃; for 1h;
  • 46
  • [ 153493-48-2 ]
  • [ 540-37-4 ]
  • <i>N</i>,<i>N</i>'-bis-(4-iodo-phenyl)-[1,2,5]oxadiazolo[3,4-<i>b</i>]pyrazine-5,6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With N,N-diethylaniline In acetonitrile Heating;
  • 47
  • [ 153493-48-2 ]
  • [ 102-28-3 ]
  • <i>N</i>-{3-[6-(3-acetylamino-phenylamino)-[1,2,5]oxadiazolo[3,4-<i>b</i>]pyrazin-5-ylamino]-phenyl}-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With N,N-diethylaniline In acetonitrile Heating;
  • 48
  • [ 153493-48-2 ]
  • [ 108-33-8 ]
  • 2-methyl-6-oxa-1-thia-3,3a,4,5,7,8,9-heptaaza-cyclopenta[<i>a</i>]-<i>s</i>-indacene [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With triethylamine In acetonitrile at 20℃; for 1h;
  • 49
  • [ 24294-89-1 ]
  • [ 153493-48-2 ]
YieldReaction ConditionsOperation in experiment
77% With phosphorus pentachloride; trichlorophosphate at 95℃; for 2h;
69% With phosphorus pentachloride; trichlorophosphate Heating;
48% With thionyl chloride In N,N-dimethyl-formamide at 5 - 75℃;
44% With phosphorus pentachloride; trichlorophosphate at 95℃; for 2h; In a flask with reflux condenser and stirring bar, a mixture of phosphorus oxychloride (5.6 mL, 64.1 mmol), phosphorus pentachloride (12.5 g, 59.8 mmol), and [1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diol (4.39 g, 28.5 mmol) was heated to 95°C for 2 h (caution: HCl development). After cooling, the condenser was replaced with a distillation bridge and POCl3 was distilled off with heating. The remaining residue was cooled in an ice bath and treated with cold water (caution: violent reaction of residual phosphorus chlorides may occur). The precipitate was filtered off and washed with two portions of cold water. The solid was largely dissolved by addition of acetone (15 mL) and then precipitated by addition of water (25 mL). The precipitate was filtered off and washed with cold water (2 x). After drying in vacuo, a beige solid (2.42 g, 12.7 mmol, 44 %) was obtained which was used without further purification.
42% With thionyl chloride In N,N-dimethyl-formamide at 10 - 75℃; for 2.3h; 3 Example 3. Synthesis of Compound 4 Compound 3 (20.0 g, 130 mmol) was suspended in thionyl chloride (150 mL), dry DMF (20 mL) was added dropwise, and the temperature of the reaction system was maintained between 10°C and 18°C. After the completion of the dropwise reaction, the reaction was performed at 20°C for 30 minutes. After heating to 75°C for 2 hours, it was cooled to room temperature and the thionyl chloride solution was poured onto a large amount of ice to wash out a large amount of white solid. It was filtered, washed with water and dried to give a white solid 4 (10.3 g, 42%).
With phosphorus pentachloride; trichlorophosphate Heating;
5.2 g With phosphorus pentachloride; trichlorophosphate at 20℃; for 0.166667h;
With phosphorus pentachloride; trichlorophosphate at 95℃; for 2h; 1 5,6-dichloro-[1,2,5]oxadiazolo[3,4-b]pyrazine (2). 1,2,5-oxadiazole-3,4-diamine (1 equiv.) was dissolved in 10% HCl (6 M solution). Oxalic acid (1.5 equiv.) was added to the solution, and the mixture was heated to reflux for 3 h. After which, the mixture was cooled to rt, filtered, and dried. The resulting dihydroxy white solid was then carried forward crude (1 equiv.) by adding phosphorous pentachloride (6 equiv.) and phosphorous oxychloride (2 M solution). The resulting mixture was heated to 95 C for 2 h, and excess phosphorous oxychloride was removed via vacuum distillation. The mixture was cooled to 0 C, and cold water was added (15-20 mL), causing the title compound to precipitate out of solution. The precipitate was purified via recrystallization using an acetone/water mixture, producing the title compound 2 as a white solid, 23%. Analytical data matches with the literature (Thottempudi, V.; et al., Chem. Eur. J.2014, 20, 542-548).

  • 50
  • [ 153493-48-2 ]
  • [ 206446-59-5 ]
YieldReaction ConditionsOperation in experiment
89% With sodium azide In water; acetone for 1h;
  • 51
  • [ 153493-48-2 ]
  • [ 109-77-3 ]
  • [ 385817-15-2 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate In acetonitrile at 20 - 50℃; for 0.2h;
  • 52
  • [ 67-56-1 ]
  • [ 870-46-2 ]
  • [ 153493-48-2 ]
  • [ 851660-37-2 ]
  • [ 851660-36-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: methanol; 5,6-dichlorofurazano<3,4-b>pyrazine With ammonia; triethylamine In tetrahydrofuran at 0℃; for 1.16667h; Stage #2: t-butoxycarbonylhydrazine In tetrahydrofuran at 0 - 20℃; In a flask with stirring bar, 5,6-dichloro-[1,2,5]oxadiazolo[3,4-b]pyrazine (0.420 g, 2.20 mmol) was dissolved in THF (2 mL). After cooling to 0°C, a solution of the appropriate amine (formula (IV); 2.00 mmol) in THF (2 mL) was added dropwise. After stirring for 10 min at 0°C, triethylamine (0.28 mL, 2.00 mmol) was added. After stirring for 1 h at 0°C, a solution of tert-butyl carbazate (formula (III); 0.291 g, 2.2 mmol) in THF (2 mL) was added followed by triethylamine (0.31 mL, 2.2 mmol). The order of adding the amine andtert-butyl carbazate may also be reversed. The mixture was stirred overnight at r.t. After removal of the solvent in vacuo, the residue was agitated with water (5 mL). The solid was filtered off and washed with water (2 x). The crude products weres purified by preparative HPLC or by recrystallisation. Yields covered a range between 20 and 80 %.; N'-(6-Methoxy-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl)-hydrazinecarboxylic acid tert-butyl ester. This compound was obtained as a second product in the course of the preparation of N'-(6-amino-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl)-hydrazinecarboxylic acid tert-butyl ester. 1H NMR: δ = 1.43 (s, 9 H), 4.12 (s, 3 H), 9.34 (s, br., 1 H), 10.42 (s, br., 1 H). LC/(+)-ESI-MS: m/z = 283 [M+H]+, 268 [283-CH3]+, 227 [283-isobutene]+, 183 [227-CO2]+. LC/(-)-ESI-MS: m/z= 281 [M-H]-, 207 [281-t-BuOH]-.
  • 53
  • [ 464913-11-9 ]
  • [ 473732-94-4 ]
  • [ 153493-48-2 ]
  • C21H23N7O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
9.6% To a stirred solution of the commercially available 5, 6-Dichloro- [1 , 2, 5]oxadiazolo[3,4-b]pyrazine 2 in anhydrous acetonitrile was added the furyl amine 3 and stirred overnight at room temperature. The crude reaction mixture was then treated with the phenolic amine 1 and stirring was continued for another 12 hours. The solvent was removed and the product was purified by preparative thin layer chromatography using dichloromethane and methanol (20:1) to obtain the diamino compound 4 (Yield = 9.6%, M+1 = 438.1 ). Compound 4 had a CXCR2 K1 of 196 nM, and a CXCR1 K1 of 4.22 muM.
  • 54
  • [ 29364-29-2 ]
  • [ 153493-48-2 ]
  • [ 1355353-80-8 ]
YieldReaction ConditionsOperation in experiment
87% In tetrahydrofuran at -20 - -5℃;
  • 55
  • [ 153493-48-2 ]
  • [ 202207-24-7 ]
YieldReaction ConditionsOperation in experiment
97% With ammonium hydroxide In acetonitrile at 5 - 20℃; for 2.5h;
  • 56
  • [ 17003-75-7 ]
  • [ 153493-48-2 ]
  • 5,6-bis(2-fluoro-2,2-dinitroethoxy)furazano[3,4-b]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
89.3% With sodium phosphate dodecahydrate In acetone at 25℃; for 8h;
  • 57
  • [ 348-54-9 ]
  • [ 62-53-3 ]
  • [ 153493-48-2 ]
  • N5-(2-fluorophenyl)-N6-phenyl[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% Stage #1: 2-Fluoroaniline; 5,6-dichlorofurazano<3,4-b>pyrazine With triethylamine In tetrahydrofuran at 0℃; for 1h; Stage #2: aniline With triethylamine at 20℃; for 19h; 1 Synthesis of asymmetrical diarylamine analogs General procedure: 5,6-Dichloro-[1,2,5]oxadiazolo[3,4-b]pyrazine (2, 1 equiv.) was dissolved in THF (0.52 M solution) and cooled to 0 C. The desired substituted arylamines (0.9 equiv.) was then added dropwise and allowed to stir for 10 min. Triethylamine (1 equiv.) was then added dropwise and allowed to stir at 0 qC for 1 h. The second desired substituted arylamine was then added dropwise and allowed to stir for 10 min. Triethylamine (1 equiv.) was then added dropwise, and the reaction was then allowed to warm to room temperature and allowed to stir for 19 h. After which, the solution was concentrated via vacuum, and the residue was purified by silica gel column chromatography to yield an asymmetrical arylamine, 4; Synthesized by general procedure B.44%, yellow solid. 1H NMR (400 MHz, Acetone-d6) 11.44- 9.05 (brm, 2H), 7.76 (brs, 3H), 7.45 (t, J = 7.8 Hz, 2H), 7.35- 7.14 (m, 4H); 19F NMR (376 MHz, Acetonitrile-d3) -122.05- -130.05 (m, 1F); HRMS (ESI+): Calcd for C16H12FN6O + [M+H]+: 323.1057, Found: 323.1051.
  • 58
  • [ 348-54-9 ]
  • [ 153493-48-2 ]
  • C10H5ClFN5O [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran for 16h; Reflux; 1 Unsymmetric Alkylamine and Arylamine Derivative Synthesis General procedure: 5,6-Dichloro-[1,2,5]oxadiazolo[3,4-b]pyrazine (2, 1 equiv.) was dissolved in THF (0.6 M solution). The desired arylamine (2 equiv.) was then added. The reaction mixture was allowed to reflux for 16 h. After which, the solution was concentrated via vacuum, and the residue was purified via flash chromatography using dichloromethane/methanol solvent system to obtain the monoaminated intermediate. The intermediate was in turn dissolved in THF (0.6 M). The desired alkylamine was added dropwise at room temperature and allowed to stir for 1 h. The resulting reaction mixture was then concentrated via vacuum, and the resulting residue was purified via flash chromatography using dichloromethane/methanol solvent system to obtain the asymmetrical arylamine/alkylamine compound, 7; Synthesized using General Procedure C. 1H NMR (CDCl3, 400 MHz) 8.19- 7.85 (m, 1H), 7.77- 7.37 (m, 1H), 7.30- 7.19 (m, 1H), 3.15 (s, 3H). HRMS (ESI+) m/z calcd for C11H10FN6O [M+H]+: 261.0895 Found: 261.0893
With triethylamine In tetrahydrofuran at 0℃;
  • 59
  • [ 461-82-5 ]
  • [ 153493-48-2 ]
  • [ 156-87-6 ]
  • 3-((6-((4-(trifluoromethoxy)phenyl)amino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl)amino)propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% Stage #1: 4-(trifluoromethoxy)aniline; 5,6-dichlorofurazano<3,4-b>pyrazine With triethylamine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Cooling with ice; Stage #2: propan-1-ol-3-amine In tetrahydrofuran for 2h; Inert atmosphere; 1 3-((6-((4-(Trifluoromethoxy)phenyl)amino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5- yl)amino)propan-1-ol (7h). A round-bottom flask containing 5,6-dichloro-[1,2,5]oxadiazolo[3,4- b]pyrazine (2, 0.200 g, 1.05 mmol) was evacuated and refilled with N2 (3x). The flask was placed in an ice bath and the solid was diluted sequentially with anhydrous THF (2 mL), 4-(trifluoromethoxy)aniline (0.13 mL, 0.97 mmol), and Et3N (0.15 mL, 1.1 mmol). The mixture was stirred for 2 h while slowly warming to room temperature. Then, 3-aminopropan-1-ol (0.16 mL, 2.2 mmol) was added and stirring was continued for 2 h. The mixture was concentrated and purified by chromatography on SiO2 (gradient: 0-5% MeOH/CH2Cl2) to yield the title compound (0.247 g, 69%) as a crust-like yellow solid. 1H NMR (400 MHz, Acetone-d6) 9.15 (s, 1 H), 8.07-7.56 (brm, 3H), 7.40 (d, J = 8.5 Hz, 2H), 3.82 (s, 1H), 3.75 (t, J = 6.8 Hz, 2 H), 3.71 (t, J = 6.0 Hz, 2 H), 1.97-1.90 (m, 2 H); 19F NMR (376 MHz, acetone) -58.80 (s, 3F); HRMS (ESI+): Calcd for C14H14F3N6O + 3 [M+H]+: 371.1074, Found: 371.1090.
  • 60
  • [ 455-14-1 ]
  • [ 367-12-4 ]
  • [ 153493-48-2 ]
  • 6-(2-fluorophenoxy)-N-(4-(trifluoromethyl)phenyl)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% Stage #1: 2-fluorophenol; 5,6-dichlorofurazano<3,4-b>pyrazine With sodium t-butanolate In tetrahydrofuran at 0℃; Stage #2: 4-trifluoromethylphenylamine In tetrahydrofuran for 16h; Reflux; 81 COMPOUND 1-184. SYNTHESIS OF 6-(2-LLUOROPHENOXY)-/V-(4-(TRIFLUOROMETHYL)PHENYL)- [1,2,5] OX ADIAZOLO [3,4-S]P YRAZIN-5 - AMINE (1-184) [0328] In a screw-cap vial, 1-2 (0.300 g, 1.57 mmol) was dissolved in 8 mL of anhydrous THF at 0 °C. In a separate vial, 2-fluorophenol (0.166 g, 1.73 mmol) and sodium fe/T-butoxidc (0.194 g, 1.73 mmol) were mixed in 2 mL of anhydrous THF at 0 °C. This mixture was added dropwise to the initial vial while stirring. This was followed by the addition of 4-(trifluoromethyl)aniline (0.506 g, 3.14 mmol). The mixture was refluxed and stirred for 16 h. The next day, the mixture was concentrated and purified chromatography on S1O2 to obtain 1-184 (18%) as a yellow solid: 'H NMR (400 MHz, Acetone-*) d 10.21 (brs, 1H), 8.38 (d, 2H, J = 8.4 Hz), 7.84 (d, 2H, J = 8.4 Hz), 7.56 (td, 1H, J = 7.8, 1.6 Hz), 7.53 7.36 (m, 3H); 19F NMR (376 MHz, Acetone-*) d -62.57 (s, 3F), -129.41 - -129.49 (m, IF); HRMS (ESI): Calc'd. for Ci4H9F6lN502+ [M+H]+: 519.9705, Observed: 519.9714.
  • 61
  • [ 455-14-1 ]
  • [ 402-45-9 ]
  • [ 153493-48-2 ]
  • 6-(4-(trifluoromethyl)phenoxy)-N-(4-(trifluoromethyl)phenyl)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% Stage #1: 4-hydroxybenzotrifluoride; 5,6-dichlorofurazano<3,4-b>pyrazine With sodium t-butanolate In tetrahydrofuran at 0℃; Stage #2: 4-trifluoromethylphenylamine In tetrahydrofuran for 16h; Reflux; 81 COMPOUND 1-185. SYNTHESIS OF 6-(4-(TRIFLUOROMETHYL)PHENOXY)-/V-(4- (TRIFLUOROMETHYL)PHENYL)- [1,2,5] OXADIAZOLO[3,4-5] PYRAZIN-5- AMINE (1-185) [0329] In a screw-cap vial, 1-2 (0.150 g, 0.785 mmol) was dissolved in 3 mL of anhydrous THF at 0 °C. In a separate vial, 4-(trifluoromethyl)phenol (0.127 g, 0.785 mmol) and sodium teri-butoxide (0.076 g, 0.785 mmol) were mixed in 2 mL of anhydrous THF at 0 °C. This mixture was added dropwise to the initial vial while stirring. This was followed by the addition of 4-(trifluoromethyl)aniline (0.506 g, 3.14 mmol). The mixture was refluxed and stirred for 16 h. The next day, the mixture was concentrated and purified by chromatography on S1O2 to obtain 1-185 (45%) as a yellow solid: 'H NMR (400 MHz, Acetone-*) d 10.20 (brs, 1H), 8.36 (d, 2H, J = 8.4 Hz), 7.97 (d, 2H, J = 8.4 Hz), 7.84 (d, 2H, J = 8.5 Hz), 7.73 (d, 2H, J = 8.5 Hz); 19F NMR (376 MHz, Acetone-*) d -62.62 (s, 3F), -62.72 (s, 3F); HRMS (ESI): Calc'd. for CisHioFgNsC [M+H]+: 442.0733, Observed: 442.0726.
  • 62
  • [ 67-56-1 ]
  • [ 153493-48-2 ]
  • 5-chloro-6-methoxy-[1,2,5]oxadiazolo[3,4-b]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With triethylamine In tetrahydrofuran at 21℃; 81 COMPOUND 1-138. SYNTHESIS OF 5-CHLORO-6-METHOXY-[1,2,5]OXADTAZOLO[3,4-/;]PYRAZTNE (1-138) [0286] 5,6-Dichloro-[l,2,5]oxadiazolo[3,4-Zdpyrazine (1-2) (2.00g) was dissolved in anhydrous THF (25 mL) and Et; N (1.46 mL, 1 equiv.) was added. The solution was mixed and MeOH (0.9 equiv.) was added dropwise over a few minutes. The solution evolved into a slurry and was allowed to stir at room temperature for 30 min. The solvent was then removed under reduced pressure and purified by chromatography on S1O2 (gradient: 5 - 15% EtOAc/hexanes) to yield 1-138 (68%) as a colorless solid.
  • 63
  • [ 348-54-9 ]
  • [ 75-89-8 ]
  • [ 153493-48-2 ]
  • N-(2-fluorophenyl)-6-(2,2,2-trifluoroethoxy)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% Stage #1: 2-Fluoroaniline; 5,6-dichlorofurazano<3,4-b>pyrazine With triethylamine In tetrahydrofuran for 2.5h; Inert atmosphere; Cooling with ice; Stage #2: 2,2,2-trifluoroethanol With triethylamine In tetrahydrofuran at 21℃; for 17h; Inert atmosphere; 81 COMPOUND 1-187. SYNTHESIS OF A-(2-FLUOROPHENYL)-6-(2,2,2-TRIFLUOROETHOXY)- [1,2,5] OX ADIAZOLO [3,4-S]P YRAZIN-5 - AMINE (1-187) [0330] A round-bottom flask containing 1-2 (0.21 g, 1.1 mmol) was evacuated and flushed with N2 (3x). Then, under an atmosphere of N2, the solid was cooled in an ice bath and diluted sequentially with dry THF (3 mL), 2-fluoroaniline (0.10 mL, 1.0 mmol), and EuN (0.15 mL, 1.1 mmol). The resulting red solution, cooled in an ice bath, was stirred for 2.5 h, filtered to remove the salts rinsing with EtOAc, concentrated to remove the solvents, passed through a S1O2 plug (CH2CI2), and concentrated to a crude yellow/orange solid (0.179 g). The crude solid (0.179 g) in a round-bottom flask was evacuated and refilled with N2 (3x). Then, the solid was diluted sequentially with anhydrous THF (3 mL), 2,2,2- trifluoroethanol (0.15 mL, 2.1 mmol), and EuN (0.15 mL, 1.1 mmol). The resulting mixture was stirred at rt under an atmosphere of N2 for 17 h, filtered to remove the salts rinsing with EtOAc, and concentrated to a red solid. The solid was purified by chromatography on S1O2 (gradient: 10-15% EtO Ac/hexanes) to yield 1-187 (34%) as a light yellow solid: NMR ((CD3)2CO, 500 MHz) d 9.31 (s, 1H), 8.08 (t, J = 7.8 Hz, 1H), 7.38-7.30 (m, 3 H), 5.32 (q, / = 8.5 Hz, 2 H); 13C NMR ((CD3)2CO, 125 MHz) d 156.5 (d, JCF = 247 Hz), 154.5, 152.1, 150.2, 147.8, 128.6 (d, JCF = 8.0 Hz), 126.85, 125.8 (d, JCF = 11.4 Hz), 125.5 (d, JCF = 3.8 Hz), 124.1 (q, JCF = 277 Hz), 116.6 (d, JCF = 19.6 Hz), 65.12 (q, JCF = 37.1Hz).19F NMR ((CD3)2CO, 376 MHz) d -73.7 (t, / = 8.5 Hz, 3 F), -124.6 to -124.7 (m, 1 F); HRMS (ESI) m/z calc'd. for C12H6F4N5O2 (M-H) 328.0463, found 328.0492.
  • 64
  • [ 153493-48-2 ]
  • [ 67-63-0 ]
  • 5-chloro-6-isopropoxy[1,2,5]oxadiazolo[3,4-b]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% With triethylamine In tetrahydrofuran at 45℃; for 16h; 81.1 Step 1. Synthesis of 5-Chloro-6-isopropoxy-[l,2,5]oxadiazolo[3,4-b]pyrazine (1-183-int)) [0326] In a 25 ml round bottom flask, 5,6-dichloro-[l,2,5]oxadiazolo[3,4-b]pyrazine (1-2) (0.403 g, 2.11 mmol) and LuN (0.214 g, 2.11 mmol) were dissolved in 10 mL of anhydrous THE. Isopropanol (0.127 g, 2.11 mmol) was added. The mixture was heated to 45 °C and stirred for 16 h. The mixture was concentrated and purified chromatography on S1O2 to obtain 1-183-int (19%) as a yellow solid: NMR (400 MHz, Acetone-*) d 5.58 (h, J = 6.2 Hz, 1H), 1.53 (d, J = 6.2 Hz, 6H); 13C NMR (100 MHz, Acetone-*) d 157.58, 153.76, 152.27, 151.35, 76.09, 21.66.
  • 65
  • [ 69409-98-9 ]
  • [ 153493-48-2 ]
  • N5,N6-bis(2-fluoro-4-(trifluoromethyl)phenyl)[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine [ No CAS ]
  • 66
  • [ 535-52-4 ]
  • [ 153493-48-2 ]
  • N5,N6-bis(2-fluoro-5-(trifluoromethyl)phenyl)[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine [ No CAS ]
  • 67
  • [ 1978-38-7 ]
  • [ 153493-48-2 ]
  • N5,N6-bis(2-fluorophenyl)-N5,N6-dimethyl[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine [ No CAS ]
  • 68
  • [ 866358-12-5 ]
  • [ 153493-48-2 ]
  • 6-((3-((4-(trifluoromethyl)benzyl)oxy)phenyl)amino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 3-((4-(trifluoromethyl)benzyl)oxy)aniline; 5,6-dichlorofurazano<3,4-b>pyrazine With triethylamine In tetrahydrofuran at 20℃; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃;
  • 69
  • 2-fluoro-4-hexylaniline [ No CAS ]
  • [ 153493-48-2 ]
  • 6-((2-fluoro-4-hexylphenyl)amino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: 2-fluoro-4-hexylaniline; 5,6-dichlorofurazano<3,4-b>pyrazine In tetrahydrofuran at 50℃; for 16h; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃; for 1h;
  • 70
  • 4-pentyl-2-(trifluoromethoxy)aniline [ No CAS ]
  • [ 153493-48-2 ]
  • 6-((4-pentyl-2-(trifluoromethoxy)phenyl)amino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% Stage #1: 4-pentyl-2-(trifluoromethoxy)aniline; 5,6-dichlorofurazano<3,4-b>pyrazine In tetrahydrofuran at 50℃; for 16h; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃; for 1h;
  • 71
  • [ 461-82-5 ]
  • [ 153493-48-2 ]
  • 6-((4-(trifluoromethoxy)phenyl)amino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 4-(trifluoromethoxy)aniline; 5,6-dichlorofurazano<3,4-b>pyrazine With triethylamine In tetrahydrofuran at 20℃; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃;
  • 72
  • [ 461-82-5 ]
  • [ 124-41-4 ]
  • [ 153493-48-2 ]
  • 6-methoxy-N-(4-(trifluoromethoxy)phenyl)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 4-(trifluoromethoxy)aniline; 5,6-dichlorofurazano<3,4-b>pyrazine With triethylamine In tetrahydrofuran at 20℃; Stage #2: sodium methylate In tetrahydrofuran; methanol at 20℃; for 1h;
  • 73
  • [ 98-16-8 ]
  • [ 153493-48-2 ]
  • 6-((3-(trifluoromethyl)phenyl)amino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: 3-trifluoromethylaniline; 5,6-dichlorofurazano<3,4-b>pyrazine In tetrahydrofuran at 50℃; for 16h; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃; for 1h;
  • 74
  • [ 455-14-1 ]
  • [ 153493-48-2 ]
  • 6-((4-(trifluoromethyl)phenyl)amino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: 4-trifluoromethylphenylamine; 5,6-dichlorofurazano<3,4-b>pyrazine With triethylamine In tetrahydrofuran at 20℃; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃;
  • 75
  • [ 153493-48-2 ]
  • [ 1535-73-5 ]
  • 6-((3-(trifluoromethoxy)phenyl)amino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: 5,6-dichlorofurazano<3,4-b>pyrazine; m-trifluoromethoxyaniline With triethylamine In tetrahydrofuran at 20℃; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃;
  • 76
  • [ 106-47-8 ]
  • [ 153493-48-2 ]
  • 6-((4-chlorophenyl)amino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% Stage #1: 4-chloro-aniline; 5,6-dichlorofurazano<3,4-b>pyrazine With triethylamine In tetrahydrofuran at 20℃; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃;
  • 77
  • [ 22236-10-8 ]
  • [ 153493-48-2 ]
  • 6-((4-(difluoromethoxy)phenyl)amino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 4-difluoromethoxyaniline; 5,6-dichlorofurazano<3,4-b>pyrazine With triethylamine In tetrahydrofuran at 20℃; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃;
  • 78
  • [ 713-62-2 ]
  • [ 153493-48-2 ]
  • 6-((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: 4-(1,1,2,2-tetrafluoroethoxy)benzeneamine; 5,6-dichlorofurazano<3,4-b>pyrazine With triethylamine In tetrahydrofuran at 20℃; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃;
  • 79
  • [ 153493-48-2 ]
  • [ 39065-95-7 ]
  • 6-((4-(chlorodifluoromethoxy)phenyl)amino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 5,6-dichlorofurazano<3,4-b>pyrazine; 4-[chloro(difluoro)methoxy]aniline With triethylamine In tetrahydrofuran at 20℃; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃;
  • 80
  • [ 1544-85-0 ]
  • [ 153493-48-2 ]
  • 6-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)amino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% Stage #1: 2,2-difluoro-benzo[1,3]dioxol-5-ylamine; 5,6-dichlorofurazano<3,4-b>pyrazine With triethylamine In tetrahydrofuran at 20℃; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃;
  • 81
  • [ 722-92-9 ]
  • [ 153493-48-2 ]
  • 6-((4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)amino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoro-2-propanol; 5,6-dichlorofurazano<3,4-b>pyrazine With sodium hydrogencarbonate In water; acetone at 20℃; for 18h; Stage #2: With potassium hydroxide In water; acetone at 20℃; for 2h;
  • 82
  • [ 535-52-4 ]
  • [ 153493-48-2 ]
  • 6-((2-fluoro-5-(trifluoromethyl)phenyl)amino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% Stage #1: 2-fluoro-5-(trifluoromethyl)aniline; 5,6-dichlorofurazano<3,4-b>pyrazine In tetrahydrofuran at 50℃; for 16h; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃; for 1h;
  • 83
  • [ 153493-48-2 ]
  • [ 123973-25-1 ]
  • [ 2379551-24-1 ]
YieldReaction ConditionsOperation in experiment
21% Stage #1: 5,6-dichlorofurazano<3,4-b>pyrazine; 2-fluoro-3-(trifluoromethyl)aniline In tetrahydrofuran at 50℃; for 16h; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃; for 1h;
  • 84
  • [ 131395-23-8 ]
  • [ 153493-48-2 ]
  • 6-((2-methoxy-4-(trifluoromethoxy)phenyl)amino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% Stage #1: 2-methoxy-4-(trifluoromethoxy)aniline; 5,6-dichlorofurazano<3,4-b>pyrazine With triethylamine In tetrahydrofuran at 20℃; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃;
  • 85
  • [ 4344-55-2 ]
  • [ 153493-48-2 ]
  • 6-((4-butoxyphenyl)amino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: para-butoxyaniline; 5,6-dichlorofurazano<3,4-b>pyrazine In tetrahydrofuran at 50℃; for 16h; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃; for 1h;
Same Skeleton Products
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