96042-30-7|(E)-2-(2-(4-(Dimethylamino)styryl)-6-methyl-4H-pyran-4-ylidene)malononitrile| Ambeed

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Product Details of [ 96042-30-7 ]

CAS No. :	96042-30-7
Formula :	C₁₉H₁₇N₃O
M.W :	303.36
SMILES Code :	N#CC(C#N)=C1C=C(/C=C/C2=CC=C(N(C)C)C=C2)OC(C)=C1
MDL No. :	MFCD00051341

Safety of [ 96042-30-7 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H228-H315-H319-H332-H335
Precautionary Statements:	P210-P261-P305+P351+P338
Class:	4.1
UN#:	3175
Packing Group:	Ⅱ

Application In Synthesis of [ 96042-30-7 ]

* 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.

Upstream synthesis route of [ 96042-30-7 ]
Downstream synthetic route of [ 96042-30-7 ]

[ 96042-30-7 ] Synthesis Path-Upstream 1~2

1
[ 96042-30-7 ]
[ 243641-38-5 ]
[ 445490-61-9 ]

References: [1] Patent: US2002/169200, 2002, A1, .

2
[ 503-29-7 ]
[ 96042-30-7 ]
[ 654073-32-2 ]

References: [1] Patent: US2005/267018, 2005, A1, .

[ 96042-30-7 ] Synthesis Path-Downstream 1~11

1
[ 600-00-0 ]
[ 96042-30-7 ]
[ 51746-85-1 ]
[ 484673-55-4 ]

Yield	Reaction Conditions	Operation in experiment
33%	With triethanolamine; potassium carbonate; In methanol; N,N-dimethyl-formamide;	EXAMPLE 92(l) Synthesis of 2-Methyl-2-(4-pyridin-3-yl-imidazol-1-yl)-propionic acid ethyl ester To a solution of 3-(1H-Imidazol-4-yl)-pyridine (1 eq) in DMF was added potassium carbonate (2 eq) under dry condition. After stirring for 1 hour, ethyl 2-bromoisobutyrate (5 eq) was added to the mixture. The solution was left stirring over 36 hours at room temperature. The reaction solvent was removed in vacuo and the solid was diluted with ethyl acetate washed with H2O, NaCl(sat), dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography using a solvent gradient of 97% DCM, 3% MeOH and 0.1% TEA to yield 2-Methyl-2-(4-pyridin-3-yl-imidazol-1-yl)-propionic acid ethyl ester (33%). MH+(260)

References: [1]Patent: US2003/125266,2003,A1 .

2
[ 1336-21-6 ]
[ 96042-30-7 ]
[ 18368-58-6 ]
[ 65938-77-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hypochlorite; In tetrahydrofuran;	b) To a mixture of 100 ml of 25% aqueous hydrochloric acid and 250 ml of DCM was added 18 g of 5-methyl-2-thio-pyridine. While the mixture was vigorously stirred and kept at -1 0 C. 250 ml of an aqueous solution containing 13% of sodium hypochlorite was carefully added. Upon completion of the addition, stirring was continued for 10 min. The organic layer was separated. To the aqueous layer 250 ml of DCM was added and the mixture was again treated as before with a further 250 ml batch of bleach. Upon completion of the addition, the organic layer was separated. The aqueous layer was extracted five times with 200 ml DCM. The organic layers were combined, dried over MgSO4 and evaporated. The resulting oil was dissolved in 125 ml of THF and cooled to -20 C. 25 ml of saturated aqueous ammonium hydroxide solution was slowly added. The mixture was stirred over night at room temperature. Excess of ammonia was neutralised by adding hydrochloric acid and the THF was removed in vacuo. The remaining aqueous solution was extracted three times with 150 ml of ethyl acetate. The combined organic layers were dried over MgSO4 and the solvent was evaporated. The remaining solid was recrystallized from boiling ethyl acetate to yield 13.35 g of 5-methyl-2-pyridine sulfonamide in form of beige crystals. 1H-NMR(D6-DMSO, 300 MHz): 2.37(s, 3H); 7.36(s, 2H); 7.78-7.85(m, 2H); 8.53(s, 1H); LC-MS: tR=2.32 min, [M+1]+=173.04, [M-1]-=171.10.

References: [1]Patent: US2003/87920,2003,A1 .

3
[ 3056-18-6 ]
[ 96042-30-7 ]
[ 33024-60-1 ]
[ 253126-46-4 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In methanol; ethanol; isopropyl alcohol;	2-Chloro-N-(tetrahydro-pyran-4-yl)-adenosine A mixture of acetic acid 4R-acetoxy-5R-acetoxymethyl-2R-(2,6-dichloro-purin-9-yl)-tetrahydro-furan-3R-yl ester (10 g), diisopropylethylamine (5.7 ml), and 4-amino tetrahydropyran hydrochloride (2.02 g), in isopropanol (200 ml) was heated at 50° for 4 h. The cooled mixture was evaporated in vacuo, the residue re-dissolved in methanol (200 ml) and ammonia gas bubbled through the solution for 2 h. The mixture was stirred at 22° C. overnight, and evaporated in vacuo to give a brown oily solid. Purification by flash chromatography on silica gel (Merck 9385), eluding with 75:8:1 DCM:EtOH:880 NH3 to 50:8:1 DCM:EtOH:880NH3, gave the title compound as a pale brown oily solid (7.81 g). LC/MS (System B) Rt 2.24 min. Mass spectrum m/z 3.86 [MH+].

References: [1]Patent: US6492348,2002,B1 .

4
[ 5780-37-0 ]
[ 3325-11-9 ]
[ 96042-30-7 ]
[ 146519-40-6 ]

Yield	Reaction Conditions	Operation in experiment
		5-Acetyl-1H-Benzotriazole [25] The ketone was prepared in the same manner as the benzotriazole aldehyde from <strong>[3325-11-9]5-aminobenzotriazole</strong> and acetaldoxime. Column chromatography of the crude ketone using DCM and eluding with MeOH (0-10percent) afforded the ketone in 11percent yield. Rf [A] 0.3; deltaH(400MHz; Acetone-d6) 2.68 (3H, s, CH3), 7.92 (1H, d, J 8.7, Ar-H), 8.07 (1H, d, J 8.7 Ar-H), 8.62 (1H, s, Ar-H); m/z (FAB-HR) 162.06674 [(M+H)+ calc. for C8H8N3O 162.06682]. The hydrazone of the ketone was prepared from 2,4DNPH to afford an orange solid.

References: [1]Patent: EP1272827,2008,B1 .

5
[ 33105-81-6 ]
con H₂SO₄ [ No CAS ]
[ 96042-30-7 ]
[ 115-11-7 ]
[ 99285-38-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	With NaOH; In 1,4-dioxane;	Method A2R-Amino-3,3-dimethyl-butyric acid (5.02 g, 37.2 mmol) was added to a solution of DCM (25 mL) and dioxane (25 mL) in a glass pressure tube and cooled to -30° C. in a dry ice acetone bath. con H2SO4 (2.75 mL, 41.98 mmol) was added to the solution.Isobutene (25 mL) was condensed in a dry ice bath and added to the solution.The reaction mixture was warmed to rt over 1 h, then heated to 40° C. for 2 days.Reaction was cooled to -30° C. and the vessel was opened.Adjust the solution to pH=10 with 2N NaOH.The mixture was partition between Et2O and H2O.The aqueous layer was washed with Et2O three times, and the combined organic layers were extracted with brine and dried over Na2SO4.The drying agent was removed by vacuum filtration and 2R-amino-3,3-dimethyl-butyric acid tert-butyl ester (5.12 g, 72percent) was isolated by the evaporation of solvent under reduced pressure to afford a colorless oil.LC/MS=188 (M++1)

References: [1]Patent: US2011/135599,2011,A1 .

6
[ 7768-28-7 ]
[ 7597-22-0 ]
[ 96042-30-7 ]
[ 1269626-25-6 ]

Yield	Reaction Conditions	Operation in experiment
15%	With sodium hydride; In tetrahydrofuran; n-heptane; mineral oil;	Route 4 (Route 3 See Example 12).2-[2-(4,6-Di-morpholin-4-yl-[1,3,5]triazin-2-yloxy)-ethyl]-phenol2-(2-Hydroxy-ethyl)-phenol (73 mg, 0.53 mmol) was added to a solution of 2-chloro-4,6-di-morpholin-4-yl-[1,3,5]triazine (151 mg, 0.53 mmol) in THF (3 ml) followed by sodium hydride (60percent suspension in mineral oil; 14 mg, 1.06 mmol) and the mixture was stirred at room temperature for 1 h and heated at 70° C. for 18 h.After cooling, the mixture was partitioned between water and EtOAc and the aqueous phase was extracted with EtOAc.The combined organic phases were dried (MgSO4) and concentrated in vacuo.The crude residue was purified by column chromatography with EtOAc/heptane (0-40percent gradient) as the eluent followed by trituration from DCM/heptane to give the title compound (30 mg, 15percent).

References: [1]Patent: US2012/202806,2012,A1 .

7
[ 1414960-14-7 ]
[ 18628-07-4 ]
[ 96042-30-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In 5,5-dimethyl-1,3-cyclohexadiene;	Example 7 Synthesis of Compound 29 A suspension of (3-bromophenyl)(3-(dibenzo[b,d]furan-4-yl)phenyl)diphenylsilane (2.5 g, 4.30 mmol), 9H-3,9'-bicarbazole (1.715 g, 5.16 mmol), Pd2(dba)3 (0.079 g, 0.086 mmol), SPhos (0.071 g, 0.172 mmol), and sodium tert-butoxide (0.826 g, 8.60 mmol) in xylene (50 mL) was refluxed at 140 C. under nitrogen overnight. After cooling to room temperature, the reaction was quenched with water and extracted with toluene. The organic phase was isolated, washed with water, and dried over MgSO4. Upon evaporation of the solvent, the residue was purified by column chromatography on silica gel with hexane:DCM (8:2, v/v) as eluent, precipitation from DCM to ethanol to yield Compound 29 (2.86 g, 80%) as a white solid.

References: [1]Patent: US2012/298966,2012,A1 .

8
[ 657408-07-6 ]
[ 52522-40-4 ]
3,5-bis(4-tert-butylphenyl)phenyl-1-boronic acid pinacol ester [ No CAS ]
[ 77-98-5 ]
[ 96042-30-7 ]

Yield	Reaction Conditions	Operation in experiment
	In water; ethyl acetate; toluene;	Stage 2: Stage 1 material (8.50 g) and 3,5-bis(4-tert-butylphenyl)phenyl-1-boronic acid pinacol ester (15.50 g) were dissolved in toluene (230 mL). The solution was purged with nitrogen for 1 h before 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (66 mg) and tris(dibenzylidene)dipalladium (75 mg) were added using 10 mL of nitrogen-purged toluene. A 20wtpercent solution of tetraethylammonium hydroxide in water (60 mL) was added in one portion and the mixture as stirred for 20 h with the heating bath set to 105 °C. T.L.C. analysis indicated all the stage material had been consumed and only one fluorescent spot was observed. The reaction mixture was cooled and filtered into a separating funnel. The layers were separated and the aqueous layer extracted with toluene. The organic extracts were washed with water, dried with magnesium sulphate, filtered and concentrated to yield the crude product as a yellow/orange solid. Pure compound was obtained by column chromatography eluting with a gradient of ethyl acetate in hexanes followed by precipitation from DCM/methanol. HPLC indicated a purity of 99.75percent and a yield of 80percent (11.32g). 1H NMR (referenced to CDCl3): 7.83 (3H, d), 7.76 (6H, s), 7.73 (3H, s) 7.63 (12H, d) 7.49 (12H, d), 7.21 (3H, dd), 6.88 (3H, d), 4.28 (9H, s), 2.25 (3H, m), 1.98 (3H, m), 1.4-1.5 (57H, m), 1.23 (3H, m), 0.74 (9H, t)

References: [1]Patent: EP2738195,2014,A1 .Location in patent: Page/Page column.

9
[ 123-91-1 ]
[ 72287-26-4 ]
[ 15864-32-1 ]
[ 24424-99-5 ]
[ 96042-30-7 ]
[ 564483-18-7 ]
[ 1244059-50-4 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; potassium acetate;	Step 1: tert-Butyl (6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)carbamate A 100 mL flask charged with 2-amino-6-bromobenzothiazole (2.52 g, 10.77 mmol), bis(pinacolato)diboron (5.45 g, 21.24 mmol), potassium acetate (3.28 g, 33.09 mmol), 2-(dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl (212.2 mg, 0.436 mmol), and tris(dibenylideneacetone)dipalladium chloroform complex (117.9 mg, 0.110 mmol) was evacuated and backfilled with nitrogen. 1,4-Dioxane (20.0 mL, 233 mmol) was added and the reaction mixture stirred under a nitrogen balloon at 100° C. for 1 h. To the reaction was then added [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride, complex with DCM (1:1) (285.9 mg, 0.350 mmol). After an additional 17 h the reaction mixture was cooled to room temperature, filtered through celite, rinsing with ethyl acetate, and then evaporated to dry on celite. The crude product was purified via flash chromatography on silica gel (80 g silica, solvent gradient: 0-100percent isopropyl acetate in heptanes) to yield 2.85 g. Of this material, 2.64 g was combined with di-tert-butyl dicarbonate (2.58 g, 11.45 mmol), 4-dimethylaminopyridine (79.9 mg, 0.654 mmol) and DCM (20.0 mL, 312 mmol) and stirred at room temperature for 2 h. The mixture was evaporated in vacuo and the crude product was purified via flash chromatography on silica gel (40 g silica, solvent gradient: 0-50percent ethyl acetate in heptane) to yield 2.24 g of the title compound. LCMS (ESI): [M+H]+=377.

References: [1]Patent: US2018/65983,2018,A1 .

10
[ 72287-26-4 ]
[ 1244059-50-4 ]
4-bromo-1-iodo-7,8,9,10-tetrahydro-6-oxa-2,10a-diazacycloocta[cd]indene [ No CAS ]
[ 96042-30-7 ]
tert-butyl (6-(4-bromo-7,8,9,10-tetrahydro-6-oxa-2,10a-diazacycloocta[cd]inden-1-yl)benzo[d]thiazol-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With nitrogen; sodium carbonate;	Step 2: tert-Butyl (6-(4-bromo-7,8,9,10-tetrahydro-6-oxa-2,10a-diazacycloocta[cd]inden-1-yl)benzo[d]thiazol-2-yl)carbamate A mixture of 4-bromo-1-iodo-7,8,9,10-tetrahydro-6-oxa-2,10a-diazacycloocta[cd]indene (1.0323 g, 2.6266 mmol), tert-butyl (6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)carbamate (2.031 g, 3.239 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride, complex with DCM (1:1) (324.8 mg, 0.3977 mmol), sodium carbonate (847.5 mg, 7.92 mmol), water (3.0 mL, 170 mmol) and THF (9.0 mL, 110 mmol) was heated in a sealed vessel under nitrogen at 80° C. for 20 h. The reaction mixture was degassed by bubbling through nitrogen for 10 minutes, additional [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride, complex with DCM (1:1) (523 mg) was added, and the mixture heated at 80° C. for 6 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, filtered, washed with water and brine, and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (40 g silica, solvent gradient: 0-100percent ethyl acetate in dichloromethane) to yield 0.4242 g (31percent) of the title compound as a yellow solid. LCMS (ESI): [M+H]+=514.95; 1H NMR (400 MHz, DMSO-d6) delta 11.94 (s, 1H), 8.32 (d, J=1.2 Hz, 1H), 7.84 (d, J=8.4 Hz, 1H), 7.72 (dd, J=8.3, 1.7 Hz, 1H), 7.69-7.64 (m, 1H), 7.12-7.06 (m, 1H), 4.52-4.41 (m, 2H), 4.36-4.26 (m, 2H), 2.24-2.11 (m, 2H), 1.78-1.63 (m, 2H), 1.53 (s, 9H).

References: [1]Patent: US2018/65983,2018,A1 .

11
[ 96042-30-7 ]
[ 134857-22-0 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia;	Step 3: Preparation of tert-butyl 9-aminononanoate To a solution of the compound prepared in step 2 (200 mg, 0.682 mmol) was added 7N NH3 in MeOH and stirred at 50C for 24 hours. The reaction mixture was concentrated to give an oil. The crude mixture was purified by silica gel column chromatography using MeOH/DCM = 8 % to give the title compound (48 mg, 0.209 mmol, 30 %) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 6.92 (s, 2H), 3.04 (t, J = 7.7 Hz, 2H), 2.20 (t, J = 7.5 Hz, 2H), 1.91-1.73 (m, 2H), 1.63-1.50 (m, 2H), 1.50-1.37 (m, 11H), 1.37-1.21 (m, 6H).

References: [1]Patent: EP3922632,2021,A1 .

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H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

Alternative Products

Product Details of [ 96042-30-7 ]

Safety of [ 96042-30-7 ]

Application In Synthesis of [ 96042-30-7 ]

[ 96042-30-7 ] Synthesis Path-Upstream 1~2

[ 96042-30-7 ] Synthesis Path-Downstream 1~11

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