74853-07-9

Basic information

• Product Name: 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]-3H-1,2,4-triazol-3-one
• Synonyms: 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]-3H-1,2,4-triazol-3-one;4-[4-[4-(4-Methoxyphenyl)piperazino]phenyl]-3,4-dihydro-2H-1,2,4-triazole-3-one;Posaconazole inter-5;3H-1,2,4-Triazol-3-one,2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-;4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one;2,4-DIHYDRO-4-[4-[4-(4-METHOXYPHENYL)PIPERAZIN-1-YL]PHENYL]-3H-1,2,4-TRIAZOL-3-ONE(WXC08779);4-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]-1H-1,2,4-triazol-5-one
• CAS NO: 74853-07-9
• Molecular Formula: C₁₉H₂₁N₅O₂
• Molecular Weight: 351.40234
• EINECS: 278-009-6
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 74853-07-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 270-277°C (dec.)
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 0-0Pa at 20-25℃
• Refractive Index: 1.665
• Storage Temp.: -20°C Freezer
• PKA: 10.16±0.20(Predicted)
• CAS DataBase Reference: 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]-3H-1,2,4-triazol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]-3H-1,2,4-triazol-3-one(74853-07-9)
• EPA Substance Registry System: 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]-3H-1,2,4-triazol-3-one(74853-07-9)

Safety Data

• Hazardous Substances Data: 74853-07-9(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

4-{[4-(4-Methyloxyphenyl)-piperazin-1-yl]-phenyl}-2,4-dihydro-[1,2,4]-triazol-3-one, is an intermediate for the synthesis of Itraconazole (I937500), an Antifungal.

InChI:InChI=1/C19H21N5O2/c1-26-18-8-6-16(7-9-18)23-12-10-22(11-13-23)15-2-4-17(5-3-15)24-14-20-21-19(24)25/h2-9,14H,10-13H2,1H3,(H,21,25)

Synthetic route

formamidine acetic acid (3473-63-0) + N-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}hydrazinecarboxamide (74852-89-4) → 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9)

Conditions	Yield
for 3h; Reflux;	86%
In N,N-dimethyl-formamide at 130℃; for 3h;	85%
With acetic acid In N,N-dimethyl-formamide at 80℃;
With acetic acid In N,N-dimethyl-formamide at 130℃; for 3h; Inert atmosphere;

formamidine hydrochloride (6313-33-3) + N-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}hydrazinecarboxamide (74852-89-4) → 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9)

Conditions	Yield
With sodium acetate In butan-1-ol	28%

N-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}hydrazinecarboxamide (74852-89-4) + acetamidine (143-37-3) → 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9)

Conditions	Yield
In dimethyl sulfoxide at 160℃; for 2h;	28%

1-(4-methoxyphenyl)piperazine (38212-30-5) → 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 67 percent / K2CO3 / dimethylsulfoxide / 120 °C 2: 74 percent / H2, thiophene / 5percent Pd/C / 2-methoxy-ethanol; methanol / 50 °C / Heating 3: 61 percent / pyridine / CHCl3 / 3 h 4: 63 percent / hydrazine hydrate / dioxane / 3 h / Heating 5: 28 percent / NaOAc / butan-1-ol View Scheme

4-chlorobenzonitrile (100-00-5) + hydrosulfite sodium → 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 67 percent / K2CO3 / dimethylsulfoxide / 120 °C 2: 74 percent / H2, thiophene / 5percent Pd/C / 2-methoxy-ethanol; methanol / 50 °C / Heating 3: 61 percent / pyridine / CHCl3 / 3 h 4: 63 percent / hydrazine hydrate / dioxane / 3 h / Heating 5: 28 percent / NaOAc / butan-1-ol View Scheme

4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenylamine (74852-62-3) → 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 61 percent / pyridine / CHCl3 / 3 h 2: 63 percent / hydrazine hydrate / dioxane / 3 h / Heating 3: 28 percent / NaOAc / butan-1-ol View Scheme

1-(4-methoxyphenyl)-4-(4-nitrophenyl)-piperazine (74852-61-2) → 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 74 percent / H2, thiophene / 5percent Pd/C / 2-methoxy-ethanol; methanol / 50 °C / Heating 2: 61 percent / pyridine / CHCl3 / 3 h 3: 63 percent / hydrazine hydrate / dioxane / 3 h / Heating 4: 28 percent / NaOAc / butan-1-ol View Scheme

phenyl (4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)carbamate (74853-06-8) → 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / hydrazine hydrate / dioxane / 3 h / Heating 2: 28 percent / NaOAc / butan-1-ol View Scheme

N-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}hydrazinecarboxamide + di-isopropyl ether (108-20-3) + formamidine acetic acid (3473-63-0) + 4-methyl-2-pentanone (108-10-1) → 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9)

Conditions	Yield
With dimethyl sulfoxide

Ethyl 3-bromopropionate (539-74-2) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → ethyl 3-(4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)propanoate

Conditions	Yield
Stage #1: Ethyl 3-bromopropionate With caesium carbonate In dimethyl sulfoxide at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one In dimethyl sulfoxide at 90℃; for 12h; Inert atmosphere;	100%

ethyl bromoacetate (105-36-2) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → ethyl 2-(4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)acetate

Conditions	Yield
Stage #1: ethyl bromoacetate With caesium carbonate In dimethyl sulfoxide at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one In dimethyl sulfoxide at 90℃; for 12h; Inert atmosphere;	100%

3-chloro-2-butanone (4091-39-8) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2-(1-methyl-2-oxopropyl)-3H-1,2,4-triazol-3-one (250255-72-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; toluene at 110℃; for 16h;	97%

2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) + (4S,5R)-4,5-dimethyl-1,3,2-dioxathiolane-2,2-dioxide (120293-79-0) → 2-((1S,2R)-2-hydroxy-1-methylpropyl)-4-{4-[4-(4-methoxyphenyl)-piperazin-1-yl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

Conditions	Yield
Stage #1: 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one With potassium tert-butylate In N,N-dimethyl acetamide at 100℃; for 1h; Stage #2: (4S,5R)-4,5-dimethyl-1,3,2-dioxathiolane-2,2-dioxide In N,N-dimethyl acetamide at 50 - 60℃; for 2h; Stage #3: With sulfuric acid In N,N-dimethyl acetamide at 60℃; enantioselective reaction;	84%

1-bromo-butane (109-65-9) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → 1-butyl-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one (89848-15-7)

Conditions	Yield
Stage #1: 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one With potassium carbonate In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Stage #2: 1-bromo-butane With potassium iodide In dimethyl sulfoxide at 80℃; Inert atmosphere;	73%
With potassium carbonate; potassium iodide In dimethyl sulfoxide at 80℃;	73%
With potassium hydroxide In dimethyl sulfoxide for 14h;	61%

(R)-sec-butyl 4-methylbenzenesulfonate (61530-30-1) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → (S)-2-(sec-butyl)-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (153896-47-0)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In dimethyl sulfoxide at 20℃;	73%
With potassium hydroxide In dimethyl sulfoxide at 40℃; for 96h;	51%
With 18-crown-6 ether; potassium carbonate In dimethyl sulfoxide at 20℃;	36%

(S)-(+)-1-methylpropyl p-toluenesulfonate (50896-54-3) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → (R)-2-(sec-butyl)-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (149809-44-9)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In dimethyl sulfoxide at 20℃;	73%

propyl bromide (106-94-5) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → 4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2-propyl-2,4-dihydro-3H-1,2,4-triazol-3-one (74852-92-9)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In dimethyl sulfoxide at 20℃; Inert atmosphere;	69%
With potassium hydroxide In dimethyl sulfoxide for 14h;	65%
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 20 - 110℃; for 18h; Inert atmosphere;

1-bromo-octane (111-83-1) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → 4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1-octyl-1H-1,2,4-triazol-5(4H)-one (1339803-81-4)

Conditions	Yield
Stage #1: 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one With potassium carbonate In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Stage #2: 1-bromo-octane With potassium iodide In dimethyl sulfoxide at 80℃; Inert atmosphere;	69%

Isobutyl bromide (78-77-3) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → 1-isobutyl-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one (89848-16-8)

Conditions	Yield
Stage #1: 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one With potassium carbonate In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Stage #2: Isobutyl bromide With potassium iodide In dimethyl sulfoxide at 80℃; Inert atmosphere;	67%
With potassium hydroxide In dimethyl sulfoxide for 14h;	57%

s-butyl bromide (78-76-2, 5787-31-5) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → 2-(sec-butyl)-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (252964-68-4)

Conditions	Yield
With 18-crown-6 ether for 12h;	67%
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 20 - 110℃; for 18h; Inert atmosphere;

2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → 4-{4-[4-(4-hydroxy-phenyl)-piperazin-1-yl]-phenyl}-2,4-dihydro-[1,2,4]triazol-3-one (79538-90-2)

Conditions	Yield
With hydrogen bromide Heating;	61%

2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) + 6-phenylhexyl p-toluenesulfonate (66605-85-4) → 4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1-(6-phenylhexyl)-1H-1,2,4-triazol-5(4H)-one (1339803-82-5)

Conditions	Yield
Stage #1: 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one With potassium carbonate In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Stage #2: 6-phenylhexyl p-toluenesulfonate With potassium iodide In dimethyl sulfoxide at 80℃; Inert atmosphere;	61%

toluene-4-sulphonic acid cyclopentylmethyl ester (21856-53-1) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → 1-(cyclopentylmethyl)-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one (1339803-80-3)

Conditions	Yield
Stage #1: 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one With potassium carbonate In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Stage #2: toluene-4-sulphonic acid cyclopentylmethyl ester With potassium iodide In dimethyl sulfoxide at 80℃; Inert atmosphere;	59%

2-pentyl tosylate (3813-69-2) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → 4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1-(pentan-2-yl)-1H-1,2,4-triazol-5(4H)-one (1339803-77-8)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In dimethyl sulfoxide at 20℃; Inert atmosphere;	57%

3-bromopentane (1809-10-5) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → 4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1-(pentan-3-yl)-1H-1,2,4-triazol-5(4H)-one (184177-74-0)

Conditions	Yield
Stage #1: 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one With potassium carbonate In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Stage #2: 3-bromopentane With potassium iodide In dimethyl sulfoxide at 80℃; Inert atmosphere;	56%

2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) + i-pentyl bromide (107-82-4) → 1-isopentyl-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one (1339803-78-9)

Conditions	Yield
Stage #1: 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one With potassium carbonate In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Stage #2: i-pentyl bromide With potassium iodide In dimethyl sulfoxide at 80℃; Inert atmosphere;	56%

1-Bromopentane (110-53-2) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → 4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1-pentyl-1H-1,2,4-triazol-5(4H)-one (1339803-76-7)

Conditions	Yield
Stage #1: 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one With potassium carbonate In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Stage #2: 1-Bromopentane With potassium iodide In dimethyl sulfoxide at 80℃; Inert atmosphere;	53%

Methyl 4-(bromomethyl)benzoate (2417-72-3) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → C28H29N5O4 (895136-26-2)

Conditions	Yield
With potassium carbonate In acetonitrile at 150℃; for 0.25h; Microwave heating;	49%

(4R,5R)-4,5-dimethyl-1,3,2-dioxathiolane 2,2-dioxide (106757-36-2) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → C23H28N5O5S(1-)*K(1+)

Conditions	Yield
Stage #1: 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 85℃; for 1h; Stage #2: (4R,5R)-4,5-dimethyl-1,3,2-dioxathiolane-2,2-dioxide In N,N-dimethyl-formamide at 85℃; for 18h;	48%

2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) + isopropyl bromide (75-26-3) → 1-isopropyl-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one (89848-14-6)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide for 14h;	47%

toluene-4-sulfonic acid isopropyl ester (2307-69-9) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → 1-isopropyl-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one (89848-14-6)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In dimethyl sulfoxide at 20℃; Inert atmosphere;	47%

ethyl bromide (74-96-4) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → 1-ethyl-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one (74852-95-2)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide for 14h;	44%

methyl bromide (74-83-9) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → 4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1-methyl-1H-1,2,4-triazol-5(4H)-one (74852-91-8)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide for 14h;	35%

2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) + ethyl ester of p-toluenesulfonic acid (80-40-0) → 1-ethyl-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one (74852-95-2)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In dimethyl sulfoxide at 20℃; Inert atmosphere;	32%

C18H21BrO5S + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → C31H37N5O4

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 85℃; for 12h;	30%

1-bromocyclohexane (108-85-0) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → 1-cyclohexyl-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one (1339803-79-0)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In dimethyl sulfoxide at 20℃; Inert atmosphere;	24%

Upstream product

• 38212-30-5 4-(4-methoxyphenyl)piperazine 
• 74852-89-4 N-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}hydrazinecarboxamide 
• 143-37-3 acetamidine 
• 108-20-3 di-isopropyl ether 
• 3473-63-0 formamidine acetic acid 
• 108-10-1 4-methyl-2-pentanone 
• 6313-33-3 formamidine hydrochloride 
• 74853-06-8 phenyl (4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)carbamate 
• 74852-61-2 1-(4-methoxyphenyl)-4-(4-nitrophenyl)-piperazine 
• 74852-62-3 4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenylamine 
• 100-00-5 4-chlorobenzonitrile 

Downstream Products

• 74852-91-8 4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1-methyl-1H-1,2,4-triazol-5(4H)-one 
• 74852-95-2 1-ethyl-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one 
• 79538-92-4 4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1-methyl-1H-1,2,4-triazol-5(4H)-one 
• 74853-20-6 1-ethyl-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one 
• 79538-91-3 4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-2-propyl-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 89848-19-1 4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1-isopropyl-1H-1,2,4-triazol-5(4H)-one 
• 89848-21-5 4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1-isobutyl-1H-1,2,4-triazol-5(4H)-one 
• 89848-20-4 1-butyl-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one 
• 89872-80-0 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-methyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-29-3 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-ethyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-43-1 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-methyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-30-6 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-propyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-45-3 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-ethyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-49-7 cis-4-<4-<4-<4-<<2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl>methoxy>phenyl>-1-piperazinyl>phenyl>-2,4-dihydro-2-(1-methylethyl)-3H-1,2,4-triazol-3-one 

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