79098-75-2

Usage

Uses

Used in Pharmaceutical Industry:
3-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one is used as a histamine H3 receptor antagonist for its potential therapeutic applications in cognitive disorders. Its ability to modulate neurotransmitter release and improve cognitive function makes it a promising candidate for the treatment of Alzheimer's disease and schizophrenia.
Used in Neuroprotection and Anti-inflammatory Applications:
Research suggests that PD146176 may possess anti-inflammatory and neuroprotective effects, which could contribute to its potential as a therapeutic agent in the treatment of neurological conditions. These properties may help in reducing inflammation and protecting neurons from damage, further supporting its development as a potential therapeutic agent.

InChI:InChI=1/C13H17N3O/c17-13-15-12-4-2-1-3-10(12)9-16(13)11-5-7-14-8-6-11/h1-4,11,14H,5-9H2,(H,15,17)

Synthetic route

1-benzyl-4-(1,2,3,4-tetrahydro-2-oxo-3-quinazolinyl)piperidine (79098-88-7) → 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol for 48h;	100%
With hydrogen; Pd/C In ethanol at 60℃; under 1500.15 Torr;	85%
With hydrogen; palladium on activated charcoal In ethanol at 60℃; under 1500.15 Torr;	85%

tert-butyl 4-(2-oxo-1,2,3,4-tetrahydroquinazolin-3-yl)piperidine-1-carboxylate (960221-97-0) → 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃;	92%

2-nitro-benzaldehyde (552-89-6) → 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; methanol 2: hydrogen / palladium on activated charcoal / ethanol 3: acetonitrile / Reflux View Scheme

4-amino-1-benzylpiperidine (50541-93-0) → 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; methanol 2: hydrogen / palladium on activated charcoal / ethanol 3: acetonitrile / Reflux View Scheme
Multi-step reaction with 5 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 5 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 20 h / 0 - 20 °C 3: lithium aluminium tetrahydride / 1,4-dioxane / 3 h / Reflux 4: tetrahydrofuran / 5 h / 20 °C 5: hydrogen; palladium 10% on activated carbon / methanol / 48 h View Scheme

2-amino-N-[1-(phenylmethyl)-4-piperidinyl]-benzenemethanamine (79099-03-9) + 1,1'-carbonyldiimidazole (530-62-1) → 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2)

Conditions	Yield
Stage #1: 2-amino-N-[1-(phenylmethyl)-4-piperidinyl]-benzenemethanamine; 1,1'-carbonyldiimidazole In acetonitrile Reflux; Stage #2: With hydrogen; palladium(II) hydroxide In methanol

(1-benzyl-piperidin-4-yl)-(2-nitro-benzyl)-amine (98754-28-0) → 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / palladium on activated charcoal / ethanol 2: acetonitrile / Reflux View Scheme

[2-(1-benzyl-piperidin-4-ylcarbamoyl)phenyl] tert-butyl carbamate → 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: trifluoroacetic acid / dichloromethane / 20 h / 0 - 20 °C 2: lithium aluminium tetrahydride / 1,4-dioxane / 3 h / Reflux 3: tetrahydrofuran / 5 h / 20 °C 4: hydrogen; palladium 10% on activated carbon / methanol / 48 h View Scheme

2-amino-N-(1-benzyl-piperidin-4-yl)-benzamide (83425-16-5) → 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / 1,4-dioxane / 3 h / Reflux 2: tetrahydrofuran / 5 h / 20 °C 3: hydrogen; palladium 10% on activated carbon / methanol / 48 h View Scheme

2-amino-N-[1-(phenylmethyl)-4-piperidinyl]-benzenemethanamine (79099-03-9) → 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 5 h / 20 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 48 h View Scheme

2-(tert-butyloxycarbonylamino)benzoic acid (68790-38-5) → 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2)

Conditions

Yield

Multi-step reaction with 5 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 5 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 20 h / 0 - 20 °C 3: lithium aluminium tetrahydride / 1,4-dioxane / 3 h / Reflux 4: tetrahydrofuran / 5 h / 20 °C 5: hydrogen; palladium 10% on activated carbon / methanol / 48 h View Scheme

tert-butyl 4-((2-aminobenzyl)amino)piperidine-1-carboxylate (79098-98-9) → 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / acetonitrile / 18 h / 20 °C / Reflux 2: trifluoroacetic acid / dichloromethane / 20 °C View Scheme

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 48 h / 20 °C 2: triethylamine / acetonitrile / 18 h / 20 °C / Reflux 3: trifluoroacetic acid / dichloromethane / 20 °C View Scheme

2-amino-1-benzylamine (4403-69-4) → 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 48 h / 20 °C 2: triethylamine / acetonitrile / 18 h / 20 °C / Reflux 3: trifluoroacetic acid / dichloromethane / 20 °C View Scheme

1,1'-Carbonyl-di-(1,2,4-triazole) (41864-22-6) + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) + 2-Amino-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester; hydrochloride (61039-29-0) → C24H26Br2N4O5

Conditions	Yield
With triethylamine In tetrahydrofuran	100%

1,1'-Carbonyl-di-(1,2,4-triazole) (41864-22-6) + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) + methyl 2-amino-3-(3-methoxyphenyl)propanoate hydrochloride → C25H30N4O5

Conditions	Yield
With triethylamine In tetrahydrofuran	100%

1,1'-Carbonyl-di-(1,2,4-triazole) (41864-22-6) + C8H12N2O2S*ClH + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → C22H27N5O4S

Conditions	Yield
With triethylamine In tetrahydrofuran	100%

1,1'-Carbonyl-di-(1,2,4-triazole) (41864-22-6) + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) + 3-Nitro-phenylalanin-methylester-hydrochlorid → C24H27N5O6

Conditions	Yield
With triethylamine In tetrahydrofuran	100%

C13H13F3O4 + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → C26H28F3N3O4

Conditions	Yield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran	100%

3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) + (+/-)-4-(3,4-dimethoxyphenyl)-3-methoxycarbonylbutanoic acid (78647-52-6) → C27H33N3O6

Conditions	Yield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran	100%

β-(methoxycarbonyl)-1-naphthalenebutanoic acid (122872-06-4) + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → C29H31N3O4

Conditions	Yield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran	100%

3,5-dimethyl-4-hydroxy-β-(methoxycarbonyl)-benzenebutanoic acid + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → C27H33N3O5

Conditions	Yield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran	100%

1-(methoxycarbonyl)-2-(2-((2-(trimethylsilyl)ethoxy)methyl)-7-methyl-2H-indazol-5-yl)ethyl 4-nitrophenyl carbonate (855778-81-3) + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → 1-(Methoxycarbonyl)-2-(2-((2-(trimethylsilyl)ethoxy)methyl)-7-methyl-2H-indazol-5-yl)ethyl 4-(1,2-dihydro-2-oxoquinazolin-3(4H)-yl)piperidine-1-carboxylate (865626-65-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 48h;	100%
With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 48h;	100%

(R)-methyl 2-amino-3-(7-methyl-1H-indazol-5-yl)propanoate (890044-58-3) + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → (R)-methyl-2-(4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidine-1-carboxamido)-3-(7-methyl-1H-indazol-5-yl)propanoate (890044-59-4)

Conditions	Yield
Stage #1: methyl (R)-2-amino-3-(7-methyl-1H-indazol-5-yl)propanoate With di(succinimido) carbonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In N,N-dimethyl-formamide for 24h;	100%

3,5-dibromo-4-hydroxy-β-(methoxycarbonyl)-benzenebutanoic acid (204695-24-9) + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → C25H27Br2N3O5

Conditions	Yield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In tetrahydrofuran; N,N-dimethyl-formamide	98%

3,5-dibromo-4-hydroxy-β-(methoxycarbonyl)-benzenebutanoic acid (204695-24-9) + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → C25H27Br2N3O5

Conditions	Yield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran	98%

3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → (S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-butyric acid methyl ester (688020-82-8)

Conditions

Yield

Stage #1: (S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-succinic acid 1-methyl ester With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethylformamide) at 20℃; for 1h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In DMF (N,N-dimethylformamide) at 20℃; Stage #3: With potassium carbonate; citric acid more than 3 stages;

98%

3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → 3-(4-bromo-3-methyl-phenyl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-carbonyl]-amino}-propionic acid ethyl ester (688021-09-2)

Conditions	Yield
Stage #1: 2-amino-3-(4-bromo-3-methyl-phenyl)-propionic acid ethyl ester hydrochloride With 1,1'-Carbonyl-di-(1,2,4-triazole); triethylamine In DMF (N,N-dimethylformamide) at 0 - 20℃; for 2h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In DMF (N,N-dimethylformamide) at 80℃; for 1.5h;	97%

1,1'-Carbonyl-di-(1,2,4-triazole) (41864-22-6) + 2-amino-3-(3,4-diethyl-phenyl)-propionic acid methylester (600725-39-1) + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → 3-(3,4-diethyl-phenyl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-carbonyl]-amino}-propionic acid methylester (686297-92-7)

Conditions	Yield
Stage #1: 1,1'-Carbonyl-di-(1,2,4-triazole); 2-amino-3-(3,4-diethyl-phenyl)-propionic acid methylester With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 10℃; for 1.5h; Stage #2: In DMF (N,N-dimethyl-formamide) for 0.5h; Stage #3: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one for 10h; Heating / reflux;	97%

(5-bromouracil)acetic acid (31385-63-4) + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → 5-bromo-1-{2-oxo-2-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-ethyl}-1H-pyrimidine-2,4-dione

Conditions	Yield
Stage #1: (5-bromouracil)acetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In N,N-dimethyl-formamide at 20℃; for 18h;	97%

(+/-)-2-Amino-3-(7-chloro-1H-indazol-5-yl)-propionic acid methyl ester (635712-47-9) + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) + 1,1'-carbonyldiimidazole (530-62-1) → (+/-)-3-(7-chloro-1H-indazol-5-yl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid methyl ester (635710-82-6)

Conditions	Yield
Stage #1: (+/-)-2-Amino-3-(7-chloro-1H-indazol-5-yl)-propionic acid methyl ester; 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 0.25h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In tetrahydrofuran at 20℃;	94%
In tetrahydrofuran

C17H20Br2O7 + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → C30H35Br2N3O7

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In tetrahydrofuran; N,N-dimethyl-formamide	93%

C16H16O4 + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → C29H31N3O4

Conditions	Yield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran	92%

(+/-)-2-Amino-3-(7-ethyl-1H-indazol-5-yl)-propionic acid methyl ester (635712-52-6) + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) + 1,1'-carbonyldiimidazole (530-62-1) → (+/-)-3-(7-ethyl-1H-indazol-5-yl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid methyl ester (635710-84-8)

Conditions	Yield
Stage #1: (+/-)-2-Amino-3-(7-ethyl-1H-indazol-5-yl)-propionic acid methyl ester; 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 0.333333h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In tetrahydrofuran at 20℃;	92%
In tetrahydrofuran

1,1'-Carbonyl-di-(1,2,4-triazole) (41864-22-6) + C10H11Br2NO2*ClH + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → C24H26Br2N4O4

Conditions	Yield
With triethylamine In tetrahydrofuran	90%

(R)-2-amino-3-[1-(2-trimethylsilanyl-ethanesulfonyl)-1H-indazol-5-yl]-propionic acid methyl ester (635713-85-8) + di(succinimido) carbonate (74124-79-1) + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → (R)-2-{[4-(2-Oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-3-[1-(2-trimethylsilanyl-ethanesulfonyl)-1H-indazol-5-yl]-propionic acid methyl ester (635713-93-8)

Conditions	Yield
Stage #1: (R)-2-amino-3-[1-(2-trimethylsilanyl-ethanesulfonyl)-1H-indazol-5-yl]-propionic acid methyl ester; di(succinimido) carbonate With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.666667h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In dichloromethane at 20℃;	90%
With N-ethyl-N,N-diisopropylamine In dichloromethane	1.15 g (90%)

3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → 2-(4-chloro-3-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-butanoic acid methyl ester (688021-42-3)

Conditions	Yield
Stage #1: 2-(4-chloro-3-trifluoromethyl-benzyl)-succinic acid 1-methyl ester With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; water at 20℃; for 0.166667h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In tetrahydrofuran; water at 20℃; for 2h; Stage #3: With sodium hydrogencarbonate In water	89%

3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) + 1,1'-carbonyldiimidazole (530-62-1) + 3,5-dibromo-D-tyrosine methyl ester → (R)-N-(1-oxo-(3,4-dihydroquinazolin-2(1H)-yl)piperidinyl)-3,5-dibromotyrosine methylester

Conditions	Yield
Stage #1: 1,1'-carbonyldiimidazole; 3,5-dibromo-D-tyrosine methyl ester With 1,2,4-Triazole In DMF (N,N-dimethyl-formamide) at 10 - 20℃; for 2h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In DMF (N,N-dimethyl-formamide) at 50 - 55℃; for 1.5h;	88%
Stage #1: 1,1'-carbonyldiimidazole; 3,5-dibromo-D-tyrosine methyl ester With 1,2,4-Triazole In DMF (N,N-dimethyl-formamide) at 10 - 20℃; for 2h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In DMF (N,N-dimethyl-formamide) at 20 - 55℃; for 1.5h; Product distribution / selectivity;	88%
With 1,2,4-Triazole In N,N-dimethyl-formamide	51%

C15H22N2O2 (936572-64-4) + di(succinimido) carbonate (74124-79-1) + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → C29H37N5O4

Conditions	Yield
In dichloromethane	87%

4-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-3,3-bis-ethoxycarbonyl-butanoic acid (600725-56-2) + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → 2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-{2-oxo-2-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-ethyl}-malonic acid diethyl ester (688020-58-8)

Conditions	Yield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In tetrahydrofuran at 20℃; for 16h;	87%

3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) + 6,7-dimethoxy-4-chloroquinazoline (13790-39-1) → 3-[1-(6,7-Dimethoxy-quinazolin-4-yl)-piperidin-4-yl]-3,4-dihydro-1H-quinazolin-2-one; hydrochloride (99161-60-1)

Conditions	Yield
In methanol Heating;	86%

(+/-)-2-amino-3-(7-ethyl-3 methyl-1H-indazol-5-yl)-propionic acid methyl ester (773887-24-4) + 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one (79098-75-2) → (+/-)-3-(7-ethyl-3-methyl-1H-indazol-5-yl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid methyl ester (855776-60-2)

Conditions	Yield
Stage #1: (+/-)-2-amino-3-(7-ethyl-3 methyl-1H-indazol-5-yl)-propionic acid methyl ester; 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 0.25h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In tetrahydrofuran at 20℃;	86%

Upstream product

• 79098-88-7 1-benzyl-4-(1,2,3,4-tetrahydro-2-oxo-3-quinazolinyl)piperidine 
• 552-89-6 2-nitro-benzaldehyde 
• 50541-93-0 4-amino-1-benzylpiperidine 
• 79099-03-9 2-amino-N-[1-(phenylmethyl)-4-piperidinyl]-benzenemethanamine 
• 530-62-1 1,1'-carbonyldiimidazole 
• 98754-28-0 (1-benzyl-piperidin-4-yl)-(2-nitro-benzyl)-amine 
• 83425-16-5 2-amino-N-(1-benzyl-piperidin-4-yl)-benzamide 
• 68790-38-5 2-(tert-butyloxycarbonylamino)benzoic acid 
• 960221-97-0 tert-butyl 4-(2-oxo-1,2,3,4-tetrahydroquinazolin-3-yl)piperidine-1-carboxylate 
• 79098-98-9 tert-butyl 4-((2-aminobenzyl)amino)piperidine-1-carboxylate 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 4403-69-4 2-amino-1-benzylamine 

Downstream Products

• 635713-18-7 (L)-2-tert-butoxycarbonylamino-4-oxo-4-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-butyric acid benzyl ester 
• 79106-27-7 1-(3,4-dimethoxybenzoylmethyl)-4-[3,4-dihydro-2(1H)-quinazolinon-3-yl]-piperidine 
• 79106-31-3 1-<2-oxo-2-(3,4-dimethoxyphenyl)-1-methylethyl>-4-(1,2,3,4-tetrahydro-2-oxo-3-quinazolinyl)piperidine 
• 600724-42-3 4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-carboxylic acid {(R)-2-(4-amino-3,5-dibromo-phenyl)-1-[1-(3-dimethylaminopropyl)-5-phenyl-1H-imidazol-2-yl]-ethyl}-amide 

Relevant academic research and scientific papers

An efficient synthesis of the piperidinyl dihydroquinazolinone (PDQ) fragment of olcegepant

Olcegepant is one of the most potent and selective small molecule CGRP antagonists for the treatment of migraine headaches. Herein, we describe a new and efficient synthesis of the key piperidinyl dihydroquinazolinone (PDQ) fragment of olcegepant. PDQ plays a key role in the activity of CGRP antagonists. Primary improvements over existing methods include a high-yielding reductive amination step, greater overall yield, and operational simplicity. Coupling of PDQ to a D-tyrosine derivative effectively produced over one half of the total molecular structure of olcegepant. A unique tandem deprotection-nucleophilic addition sequence was also applied to the coupling of Fmoc-PDQ with phenyl isocyanate.

NOVEL HETEROCYCLIC COMPOUNDS AND USE THEREOF IN MEDICINE AND IN COSMETICS

The invention relates to novel heterocyclic compounds of general formula (I), as well as their pharmaceutically acceptable salts, and their enantiomers. The invention also relates to the use thereof as a medicinal product, preferably in the prevention and/or treatment of inflammatory diseases with a neurogenic component or use thereof as a cosmetic. The compounds of the present invention act as antagonists of the CGRP-R receptor.

DIPHENYLBUTYPIPERIDINE AUTOPHAGY INDUCERS

Autophagy inducing compounds, methods of their preparation and use, and kits containg said compounds are disclosed herein.

Process for preparing 1- [N2-[3,5-dibromo-N-[[4-(3,4-dihydro-2(1H)-oxoquinazolin-3-yl)-1-piperidinyl]carbonyl]-D-tyrosyl]-L-lysyl]-4-(4-pyridinyl)-piperazine

The present application relates to a process for preparing the CGRP-antagonist 1-[N2-[3,5-dibromo-N-[[4-(3,4-dihydro-2(1H)-oxoquinazolin-3-yl)-1-piperidinyl]carbonyl]-D-tyrosyl]-L-lysyl]-4-(4-pyridinyl)-piperazine of formula by means of which this compound can be prepared in large amounts, in high yields and with high purity.

METHOD FOR THE PRODUCTION OF 1-[N2-[3,5-DIBROMO-N-[[4-(3,4-DIHYDRO-2(1H)-OXOQUINAZOLINE-3-YL)-1-PIPERIDINYL]CARBONYL]-D-TYROSYL]-L-LYSYL]-4-(4-PYRIDINYL)-PIPERAZINE

The invention relates to a method for producing the CGRP antagonist 1-[N2-[3,5-dibromo-N-[[4-(3,4-dihydro-2(1H)-oxoquinazoline-3-yl)-1-piperidinyl]carbonyl]-D-tyrosyl]-L-Iysyl]-4-(4-pyridinyl)-piperazine of formula (I). The disclosed method allows said compound to be produced in great quantities, at great yields, and at a high degree of purity.

BENZODIAZEPINE CGRP RECEPTOR ANTAGONISTS

The present invention is directed to compounds of Formula I: I (where variables R1, R2, R3, R6, R7, G, J, W, X and Y are as defined herein) useful as antagonists of CGRP receptors and useful in the treatment or prevention of diseases in which the CGRP is involved, such as headache, migraine and cluster headache. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

Modified aminoacids, pharmaceuticals containing these compounds and method for their production

The present invention relates to modified amino acids of general formula wherein A, Z, X, n, m, R, R2, R3, R4and R11are defined as in claims 1 to 5, their tautomers, their diastereomers, their enantiomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, pharmaceutical compositions containing these compounds, the use thereof and processes for preparing them as well as their use for the production and purification of antibodies and as labelled compounds in RIA- and ELISA assays and as diagnostic or analytical aids in neurotransmitter research.