[ CAS No. 119192-10-8 ] {[proInfo.proName]}

Name: 119192-10-8|4-((1H-1,2,4-Triazol-1-yl)methyl)aniline|98%
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Quality Control of [ 119192-10-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 119192-10-8 ]

Product Details of [ 119192-10-8 ]

CAS No. :	119192-10-8	MDL No. :	MFCD00973306
Formula :	C₉H₁₀N₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZGLQVRIVLWGDNA-UHFFFAOYSA-N
M.W :	174.20	Pubchem ID :	821219
Synonyms :

Safety of [ 119192-10-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 119192-10-8 ]

* 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 [ 119192-10-8 ]
Downstream synthetic route of [ 119192-10-8 ]

[ 119192-10-8 ] Synthesis Path-Upstream 1~4

1
[ 119192-09-5 ]
[ 119192-10-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride In ethanol; water; ethyl acetate	2. 1-(4-Aminophenyl)methyl-1,2,4-triazole. Hydrochloride A solution of 1-(4-nitrophenyl)methyl-1,2,4-triazole (10.0 g, 49 mmol) in ethanol (50 ml), ethyl acetate (50 ml), 5N HCl (10 ml) and water (10 ml) was hydrogenated over 10percent Pd/C(1.0 g) at 40 psi, in a Parr apparatus, until an uptake of 188 psi, had been observed (approx 10 mins). The catalyst was removed by filtration through hyflo and the solvent removed under vacuum. The residue was azeotroped with ethanol (*2) to give the title-amine hydrochloride (10.6 g, 100percent). δ (360 MHz, D₂ O) 5.53 (2H, s, CH₂), 7.37-7.48 (4H, m, Ar--H), 8.12 (1H, s, Ar--H), 8.66 (1H, s, Ar--H).
100%	With hydrogenchloride In ethanol; water; ethyl acetate	2. 1-(4-Aminophenyl)methyl-1,2,4-triazole. Hydrochloride A solution of 1-(4-nitrophenyl)methyl-1,2,4-triazole (10.0 g, 49 mmol) in ethanol (50 ml), ethyl acetate (50 ml), 5N HCl (10 ml) and water (10 ml) was hydrogenated over 10percent Pd/C (1.0 g) at 40 p.s.i., in a Parr apparatus, until an uptake of 188 p.s.i., had been observed (approx 10 mins). The catalyst was removed by filtration through hyflo and the solvent removed under vacuum. The residue was azeotroped with ethanol (*2) to give the titleamine hydrochloride (10.6 g, 100percent). δ (360 MHz, D₂ O) 5.53 (2H, s, CH₂), 7.37-7.48 (4H, m, Ar-H), 8.12 (1H, s, Ar-H), 8.66 (1H, s, Ar-H).

Reference： [1] Patent: US5567726, 1996, A,
[2] Patent: US5298520, 1994, A,
[3] Farmaco, 1989, vol. 44, # 9, p. 831 - 841
[4] European Journal of Medicinal Chemistry, 1989, vol. 24, # 5, p. 537 - 540
[5] Patent: US5567819, 1996, A,
[6] Patent: WO2007/54979, 2007, A1, . Location in patent: Page/Page column 4; 8-9
[7] Patent: WO2006/137083, 2006, A1, . Location in patent: Abstract

2
[ 6085-99-0 ]
[ 119192-10-8 ]

Reference： [1] European Journal of Medicinal Chemistry, 1989, vol. 24, # 5, p. 537 - 540

3
[ 100-11-8 ]
[ 119192-10-8 ]

Reference： [1] European Journal of Medicinal Chemistry, 1989, vol. 24, # 5, p. 537 - 540

4
[ 142-04-1 ]
[ 74205-82-6 ]
[ 101-77-9 ]
[ 119192-10-8 ]

Reference： [1] Heterocycles, 1994, vol. 38, # 8, p. 1813 - 1822

[ 119192-10-8 ] Synthesis Path-Downstream 1~5

1
[ 142-04-1 ]
[ 74205-82-6 ]
[ 101-77-9 ]
[ 119192-10-8 ]

Reference： [1]Heterocycles,1994,vol. 38,p. 1813 - 1822

2
[ CAS Unavailable ]
[ 145202-66-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 91 percent / ICl, CaCO₃ / methanol; H₂O 2: 1.) 2 molpercent Pd(OAc)2, Na₂CO₃; 2.) HCl / 1.) DMF, 100 deg C; 2.) MeOH 3: Et₃N / tetrahydrofuran 5: 95 percent / propan-2-ol; various solvent(s)
	Multi-step reaction with 5 steps 1.1: hydrogenchloride / methanol; water / 5 °C 2.1: hydrogenchloride; sodium nitrite / water / 0.5 h / -5 °C 3.1: water; sodium sulfite / 2 h / 10 - 70 °C 4.1: sulfuric acid / 2 h / 65 - 70 °C 4.2: 3 - 4 h / 20 - 70 °C 4.3: 15 - 20 °C / pH 8.5 - 9 5.1: ethanol; tert-butyl methyl ether / 1 h

Reference： [1]Chen, Cheng-Yi; Lieberman, David R.; Larsen, Robert D.; Reamer, Robert A.; Verhoeven, Thomas R.; Reider, Paul J.; Cottrell, Ian F.; Houghton, Peter G. [Tetrahedron Letters, 1994, vol. 35, # 38, p. 6981 - 6984]
[2]Current Patent Assignee: VIATRIS INC - WO2008/149152, 2008, A1

3
[ 119192-10-8 ]
[ 144034-80-0 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 6981 - 6984
[2]Tetrahedron Letters,2014,vol. 55,p. 3938 - 3941
[3]Patent: WO2008/149152,2008,A1

4
[ 936092-53-4 ]
[ 119192-10-8 ]
N-tert-butyl-3-[5-methyl-2-(4-[1,2,4]triazol-1-ylmethyl-phenylamino)-pyrimidin-4-ylamino]-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With caesium carbonate In 1,4-dioxane; N,N-dimethyl-formamide at 160℃; for 0.333333h; Microwave irradiation;	166 [0338] A mixture of intermediate 33 (0.10 g, 0.28 mmol), 4-[l,2,4]triazol-l-ylmethyl- phenylamine (60 mg, 0.34 mmol), Pd2(dba)3 (25 mg, 0.027 mmol), Xantphos (30 mg, 0.052 mmol) and cesium carbonate (0.20 g, 0.61 mmol)jn dioxane (4 mL) was sealed in a microwave reaction tube and irradiated with microwave at 160 °C for 20 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered. The filtered solid was washed with DCM, the filtrate concentrated and the residue purified by HPLC. The corrected fractions were combined and poured into saturated NaHCO3 solution (30 mL). The combined aqueous layers were extracted with EtOAc (2 x 30 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and then taken up in minimum amount of EtOAc. Hexanes were added until solid precipitated. After filtration, the title compound was obtained as a white solid (37 mg, 27%).[0339] 1H NMR (500 MHz, DMSO-d6): δ 1.17 (s, 9H), 2.13 (s, 3H), 5.29 (s, 2H), 7.14 (d, J= 8.6 Hz, 2H), 7.46 (t, J= 7.8 Hz, IH), 7.48-7.51 (m, IH), 7.56 (s, IH), 7.63 (d, J= 8.6 Hz, 2H), 7.94 (s, IH), 7.95 (s, IH), 8.08 (s, IH), 8.13 (d, J= 8.0 Hz, IH), 8.59 (s, IH), 8.60 (s, IH), 9.04 (s, IH). MS (ES+): m/z 493 (M+H)+.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2007/53452, 2007, A1 Location in patent: Page/Page column 170

5
[ 1116-77-4 ]
[ 119192-10-8 ]
[ 144034-80-0 ]

Yield	Reaction Conditions	Operation in experiment
		(ii) Preparation of crude rizatriptan benzoate; Into a clean IOOL glass reactor were charged water (20L) cone. HCl (8.5L), and l-(4- aminophenylmethyl)-l,2,4-triazole (5.0Kg). The reaction mass was stirred for 20-30min at 25-30 C and cooled to 0-5 C. Aqueous sodium nitrite (2.1Kg in 3.0Lof water) was added to the reaction mass below 5C over a period of 2hr. The reaction mass was maintained below 50C for lhr.Into a clean, 200L glass reactor were charged water (30 L) and sodium sulfite (9.0 Kg) under nitrogen atmosphere at 25-30 C. The resulting solution was cooled to below 10 C. Above diazonium salt solution was added to the reaction mass in 20-30 min period keeping the temperature below 10 C. The reaction mass was slowly heated to 65-7O0C over a period of 2.5-3. Ohr. After maintaining at this temperature for 2hr sulfuric acid EPO <DP n="12"/>(7.2L) was added to the reaction mixture and continued the maintenance at same temperature for 2.0-2.5 hr. The reaction mass was cooled to reach 20-25 0C.4-Dimethylaminobutyraldehyde diethyl acetal (7.8 kg) was added to the reaction mass in 30-45min keeping the temperature at 25-30 C. The reaction mass was maintained at this temperature for 4-5hr. TLC of the reaction mass indicated the absence of starting material. The reaction mass was heated to 35-400C and maintained for lhr. Temperature of the reaction mass was further raised to 60-65C and maintained for 3.5hr. The reaction mass was cooled to 20-30C and adjusted the pH of reaction mass to 6.5-7.0 with ammonia solution. Ethyl acetate (15L) was added to the reaction mass and stirred for 15- 20min and separated the organic layer. Aqueous layer pH was adjusted to 8.5-9.0 with ammonia solution. Aqueous layer was extracted with ethyl acetate (3 x 35L). Combined ethyl acetate layer was treated with activated carbon (lkg) and distilled of solvent under reduced pressure to get 4.7kg crude rizatriptan base as oil.The above crude rizatriptan base was dissolved in 18L of acetone at 25-30 0C. Benzoic acid (2.1kg) was added to the reaction mass at 25-30 C. After stirring for 45-60min at 25-30 C the reaction mixture was cooled to below 0 C and maintained for 10-12hr. The reaction mass was allowed to reach 20-25 0C and maintained for 2.5hr- before filtration. The wet cake was washed with 3.5L of acetone. Drying at 50-60 C gave 3kg of rizatriptan benzoate.; Example 4; Preparation of rizatriptan benzoate; (i) Preparation of crude rizatriptan benzoate:; Into a clean IOOL glass reactor were charged water (30L)5 cone. HCl (15kg), and l-(4- aminophenylmethyl)-l,2,4-triazole (7.5Kg). The reaction mass was stirred for 20-30min at 25-30 0C and cooled to below 0 C. Aqueous sodium nitrite (3.2Kg in 5Lof water) was added to the reaction mass below 5C over a period of 2hr. The reaction mass was maintained below 5C for lhr.Into a clean, 200L glass reactor were charged water (45 L) and sodium sulfite (13.5 Kg) under nitrogen atmosphere at 25-30 C. The resulting solution was cooled to below 10 0C. The above prepared diazonium salt solution was added to the reaction mass in 20-30 min period keeping the temperature below 10 C. The reaction mass was slowly heated to 65-70C over a period of 2.5-3.Ohr. After maintaining at this temperature for 2hr sulfuric acid (19.8kg) was added to the reaction mixture and continued the maintenance at same temperature for 2.0-2.5 hr. The reaction mass was cooled to reach 20-25 0C.4-Dimethylaminobutyraldehyde diethyl acetal (11.7 kg) was added to the reaction mass in 30-45min keeping the temperature at 25-30 0C. The reaction mass was maintained at this temperature for 4-5hr. TLC of the reaction mass indicated the absence of starting material. The reaction mass was heated to 35-40C and maintained for lhr. Temperature of the reaction mass was further raised to 60-65C and maintained for 3.5hr. The reaction mass was cooled to 20-30C and adjusted the pH of reaction mass to 6.5-7.0 with ammonia solution. Ethyl acetate (15L) was added to the reaction mass and stirred for 15-20min and separated the organic layer. Aqueous layer pH was adjusted to 8.8-9.2 with ammonia solution. Aqueous layer was extracted with ethyl acetate (3 x 45L). Combined ethyl acetate layer was treated with activated carbon (1.5kg) and distilled of solvent under reduced pressure to get 7.5kg of crude rizatriptan base as oil. EPO <DP n="14"/>The above crude rizatriptan base was dissolved in 3OL of acetone at 25-30 0C. Benzoic acid (3.5kg) was added to the reaction mass at 25-30 C. After stirring for 45-60min at 25-30 C the reaction mixture was cooled to below 0 C and maintained for 10-12hr. The reaction mass was allowed to reach 20-25 C and maintained for 2.5hr before filtration. The wet cake was washed with 5L of acetone. Drying at 50-60 0C gave 4.5kg of rizatriptan benzoate.

Reference： [1]Patent: WO2006/137083,2006,A1 .Location in patent: Abstract

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H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 119192-10-8 ] {[proInfo.proName]}

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[ 119192-10-8 ] Synthesis Path-Upstream 1~4

[ 119192-10-8 ] Synthesis Path-Downstream 1~5

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Aryls

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Triazoles

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