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2-(2-AMINO-5-BROMOBENZOYL) PYRIDINE is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

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  • 1563-56-0 Structure
  • Basic information

    1. Product Name: 2-(2-AMINO-5-BROMOBENZOYL) PYRIDINE
    2. Synonyms: 2-(2-AMINO-5-BROMOBENZOYL) PYRIDINE;(2-Amino-5-bromophenyl)(2-pyridinyl)methanone;Methanone, (2-amino-5-bromophenyl)-2-pyridinyl-;Pyridine, 2-(2-amino-5-bromobenzoyl);2-amino-5-bromobenzoylpyridine;2-(2-Amino-5-Bromobenzoyl) Pyridine 1-(2,4-Dichlorophenyl)ethanone;2-(2-Pyridylcarbonyl)-4-bromobenzeneamine;4-Bromo-2-[(2-pyridyl)carbonyl]aniline
    3. CAS NO:1563-56-0
    4. Molecular Formula: C12H9BrN2O
    5. Molecular Weight: 277.12
    6. EINECS: 216-352-5
    7. Product Categories: (intermediate of bromazepam);Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
    8. Mol File: 1563-56-0.mol
  • Chemical Properties

    1. Melting Point: 98-100℃
    2. Boiling Point: 451℃
    3. Flash Point: 227℃
    4. Appearance: Yellow solid
    5. Density: 1.546
    6. Vapor Pressure: 2.48E-08mmHg at 25°C
    7. Refractive Index: 1.658
    8. Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
    9. Solubility: DMSO (Slightly), Methanol (Sparingly)
    10. PKA: 2.66±0.10(Predicted)
    11. CAS DataBase Reference: 2-(2-AMINO-5-BROMOBENZOYL) PYRIDINE(CAS DataBase Reference)
    12. NIST Chemistry Reference: 2-(2-AMINO-5-BROMOBENZOYL) PYRIDINE(1563-56-0)
    13. EPA Substance Registry System: 2-(2-AMINO-5-BROMOBENZOYL) PYRIDINE(1563-56-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1563-56-0(Hazardous Substances Data)

1563-56-0 Usage

Chemical Properties

Yellow Solid

Uses

Intermediate in the preparation of Bromazepam.

Check Digit Verification of cas no

The CAS Registry Mumber 1563-56-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,6 and 3 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1563-56:
(6*1)+(5*5)+(4*6)+(3*3)+(2*5)+(1*6)=80
80 % 10 = 0
So 1563-56-0 is a valid CAS Registry Number.
InChI:InChI=1/C12H9BrN2O/c13-8-4-5-10(14)9(7-8)12(16)11-3-1-2-6-15-11/h1-7H,14H2

1563-56-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(2-Amino-5-bromobenzoyl)pyridine

1.2 Other means of identification

Product number -
Other names (2-Amino-5-bromophenyl)(pyridin-2-yl)methanone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1563-56-0 SDS

1563-56-0Synthetic route

2-(5-bromo-2-hydroxybenzoyl)pyridine
162271-31-0

2-(5-bromo-2-hydroxybenzoyl)pyridine

2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
Stage #1: 2-(5-bromo-2-hydroxybenzoyl)pyridine With 2-bromo-2-methylpropanamide; sodium hydroxide In N,N-dimethyl acetamide at 20 - 50℃; for 4h;
Stage #2: With water for 4h; Reflux;
95.6%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
Stage #1: 2-bromo-pyridine; n-butyllithium In diethyl ether; hexane at -40℃; for 1.5h;
Stage #2: 5-Bromo-2-aminobenzoic acid In tetrahydrofuran; diethyl ether; hexane at 0℃; for 2h;
Stage #3: With hydrogenchloride; sodium hydroxide; chloro-trimethyl-silane more than 3 stages;
89.3%
Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran at -40℃;
Stage #2: 5-Bromo-2-aminobenzoic acid In tetrahydrofuran at -40 - 0℃; for 2h;
Stage #3: With chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 0.5h;
62.7%
Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran at -40℃; for 1.25h;
Stage #2: 5-Bromo-2-aminobenzoic acid In tetrahydrofuran at 0℃; for 2h;
62.7%
Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran at -40℃; for 1h; Inert atmosphere;
Stage #2: 5-Bromo-2-aminobenzoic acid In tetrahydrofuran at 0 - 10℃; for 3h; Inert atmosphere;
50.7%
5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran at -40℃;
Stage #2: 5-Bromo-2-aminobenzoic acid In tetrahydrofuran at 0℃;
58%
bromazepam
1812-30-2

bromazepam

2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
With intestinal microflora (human) In N,N-dimethyl-formamide at 37℃; for 5h;
With acid
With hydrogenchloride In methanol; water for 3h; Reagent/catalyst; Darkness; Reflux;
bromazepam
1812-30-2

bromazepam

A

2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

B

glycine
56-40-6

glycine

Conditions
ConditionsYield
With hydrogenchloride at 25℃; Rate constant; Mechanism; also in micellar system;
C24H17Br2N5

C24H17Br2N5

2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
With hydrogenchloride at 90℃; for 1h;
4‑bromo‑2‑(bromomethyl)‑1‑((2‑methoxyethoxy)methoxy)benzene

4‑bromo‑2‑(bromomethyl)‑1‑((2‑methoxyethoxy)methoxy)benzene

2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: magnesium; triethylamine / tetrahydrofuran / 20 °C
1.2: 20 h / pH 1 / Reflux
1.3: pH 1
2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 6 h / 75 °C / Inert atmosphere
3.1: tert.-butylhydroperoxide; iodine; pyridine / water / 6 h / 80 °C
4.1: titanium tetrachloride / dichloromethane / 4 h / 20 °C
5.1: sodium hydroxide; 2-bromo-2-methylpropanamide / N,N-dimethyl acetamide / 4 h / 20 - 50 °C
5.2: 4 h / Reflux
View Scheme
5-bromo-2-(((2-methoxyethoxy)methoxy)benzyl)boronic acid

5-bromo-2-(((2-methoxyethoxy)methoxy)benzyl)boronic acid

2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 6 h / 75 °C / Inert atmosphere
2.1: tert.-butylhydroperoxide; iodine; pyridine / water / 6 h / 80 °C
3.1: titanium tetrachloride / dichloromethane / 4 h / 20 °C
4.1: sodium hydroxide; 2-bromo-2-methylpropanamide / N,N-dimethyl acetamide / 4 h / 20 - 50 °C
4.2: 4 h / Reflux
View Scheme
2-(5-bromo-2-(((2-methoxyethoxy)methoxy)benzyl)pyridine)

2-(5-bromo-2-(((2-methoxyethoxy)methoxy)benzyl)pyridine)

2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tert.-butylhydroperoxide; iodine; pyridine / water / 6 h / 80 °C
2.1: titanium tetrachloride / dichloromethane / 4 h / 20 °C
3.1: sodium hydroxide; 2-bromo-2-methylpropanamide / N,N-dimethyl acetamide / 4 h / 20 - 50 °C
3.2: 4 h / Reflux
View Scheme
4-bromo-2-(hydroxymethyl)phenol
5532-69-4

4-bromo-2-(hydroxymethyl)phenol

2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: triethylamine / dichloromethane / 6 h / 25 °C
2.1: magnesium; triethylamine / tetrahydrofuran / 20 °C
2.2: 20 h / pH 1 / Reflux
2.3: pH 1
3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 6 h / 75 °C / Inert atmosphere
4.1: tert.-butylhydroperoxide; iodine; pyridine / water / 6 h / 80 °C
5.1: titanium tetrachloride / dichloromethane / 4 h / 20 °C
6.1: sodium hydroxide; 2-bromo-2-methylpropanamide / N,N-dimethyl acetamide / 4 h / 20 - 50 °C
6.2: 4 h / Reflux
View Scheme
2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

2-bromo-N-(4-bromo-2-(pyridin-2-ylcarbonyl)phenyl)acetamide
1694-64-0

2-bromo-N-(4-bromo-2-(pyridin-2-ylcarbonyl)phenyl)acetamide

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane at 0℃; for 2h;100%
With sodium hydrogencarbonate In dichloromethane at 0 - 20℃;
With sodium hydrogencarbonate In dichloromethane Inert atmosphere;
2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

chloroacetyl chloride
79-04-9

chloroacetyl chloride

N-(4-bromo-2-picolinoylphenyl)-2-chloroacetamide
41526-21-0

N-(4-bromo-2-picolinoylphenyl)-2-chloroacetamide

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane Inert atmosphere;98.5%
With pyridine In dichloromethane at 20℃; for 0.5h;94%
(S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester
4652-65-7

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester

2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

methyl (4S)-4-(benzyloxycarbonylamino)-5-[4-bromo-2-(pyridine-2-carbonyl)aniline]-5-oxopentanoate

methyl (4S)-4-(benzyloxycarbonylamino)-5-[4-bromo-2-(pyridine-2-carbonyl)aniline]-5-oxopentanoate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at -10 - 15℃; for 48h; Temperature;93.6%
With dicyclohexyl-carbodiimide In dichloromethane at -10 - 15℃; for 48h;93.6%
(2S)-2-(fluorenyl-9-methoxycarbonylamino)-5-methoxy-5-oxopentanoic acid chloride

(2S)-2-(fluorenyl-9-methoxycarbonylamino)-5-methoxy-5-oxopentanoic acid chloride

2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

methyl (4S)-4-(fluorenyl-9-methoxycarbonylamino)-5-[4-bromo-2-(pyridin-2-carbonyl)anilino]-5-oxopentanoate

methyl (4S)-4-(fluorenyl-9-methoxycarbonylamino)-5-[4-bromo-2-(pyridin-2-carbonyl)anilino]-5-oxopentanoate

Conditions
ConditionsYield
In dichloromethane at 0 - 10℃; for 0.5h; Reflux;91.7%
L-N-Boc-Ala
15761-38-3

L-N-Boc-Ala

2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

A

(S)-{1-[4-bromo-2-(pyridine-2-carbonyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

(S)-{1-[4-bromo-2-(pyridine-2-carbonyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

B

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 8.5h;A 81%
B n/a
N-Cbz-L-Phe
1161-13-3

N-Cbz-L-Phe

2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

2-(N-carbobenzoxy-S-phenylalanyl)amino-5-bromophenyl-pyrid-2'-yl ketone
136295-73-3

2-(N-carbobenzoxy-S-phenylalanyl)amino-5-bromophenyl-pyrid-2'-yl ketone

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane for 120h; Ambient temperature;76.5%
2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

4-chloro-2,2-dimethyl-2H-benzo[e][1,3]oxazine
74405-07-5

4-chloro-2,2-dimethyl-2H-benzo[e][1,3]oxazine

[5-Bromo-2-(2,2-dimethyl-2H-benzo[e][1,3]oxazin-4-ylamino)-phenyl]-pyridin-2-yl-methanone
82562-61-6

[5-Bromo-2-(2,2-dimethyl-2H-benzo[e][1,3]oxazin-4-ylamino)-phenyl]-pyridin-2-yl-methanone

Conditions
ConditionsYield
In chloroform for 3h; Heating;70%
(2S)-2-[(tert-butoxy)carbonylamino]-4-(methoxycarbonyl)butanoic acid
45214-91-3

(2S)-2-[(tert-butoxy)carbonylamino]-4-(methoxycarbonyl)butanoic acid

2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

(S)-methyl 5-((4-bromo-2-nicotinoylphenyl)amino)-4-((tert-butoxycarbonyl)amino)-5-oxopentanoate

(S)-methyl 5-((4-bromo-2-nicotinoylphenyl)amino)-4-((tert-butoxycarbonyl)amino)-5-oxopentanoate

Conditions
ConditionsYield
Stage #1: (2S)-2-[(tert-butoxy)carbonylamino]-4-(methoxycarbonyl)butanoic acid With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: 2-amino-5-bromobenzoyl pyridine In N,N-dimethyl-formamide
69%
N-Cbz-Ala
1142-20-7

N-Cbz-Ala

2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

2-(N-carbobenzoxy-S-alanyl)amino-5-bromophenyl-pyrid-2'-yl ketone
136295-72-2

2-(N-carbobenzoxy-S-alanyl)amino-5-bromophenyl-pyrid-2'-yl ketone

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane for 120h; Ambient temperature;1.92 g
2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

N,N'-methylenebis<3-(2'-o-pyridoyl-4-bromo)phenyl>-4-imidazolidinone
76895-76-6

N,N'-methylenebis<3-(2'-o-pyridoyl-4-bromo)phenyl>-4-imidazolidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / pyridine / CH2Cl2 / 0.5 h / 20 °C
2: 2N HCl / methanol; H2O / 7 h / Heating
View Scheme
2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

4-oxo-3-(4-bromo-2-(2-pyridylcarbonyl)phenyl)imidazolidine
76895-81-3

4-oxo-3-(4-bromo-2-(2-pyridylcarbonyl)phenyl)imidazolidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / pyridine / CH2Cl2 / 0.5 h / 20 °C
2: 2N HCl / methanol; H2O / 7 h / Heating
View Scheme
2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

bromazepam
1812-30-2

bromazepam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / pyridine / CH2Cl2 / 0.5 h / 20 °C
2: 2N HCl / methanol; H2O / 7 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / dichloromethane / 0 - 20 °C
2: ammonia / methanol / 12 h / 0 - 20 °C / Reflux
View Scheme
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / dichloromethane / 2 h / 0 °C
2: ammonia / methanol / 4 h / 0 - 80 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / dichloromethane / Inert atmosphere
2: hexamethylenetetramine; ammonium acetate / isopropyl alcohol / 4 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / dichloromethane / Inert atmosphere
2: ammonia / dichloromethane; methanol / 0 - 20 °C / Inert atmosphere
View Scheme
2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

2-acetamido-7-bromo-5-(2-pyridyl)-3H-1,4-benzodiazepine

2-acetamido-7-bromo-5-(2-pyridyl)-3H-1,4-benzodiazepine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 94 percent / pyridine / CH2Cl2 / 0.5 h / 20 °C
2: 2N HCl / methanol; H2O / 7 h / Heating
3: NH4Cl / methanol; H2O / 17 h / Heating
4: pyridine / 24 h / 20 °C
View Scheme
2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

2-amino-7-bromo-5-(2-pyridyl)-3H-1,4-benzodiazepine hydrochloride

2-amino-7-bromo-5-(2-pyridyl)-3H-1,4-benzodiazepine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 94 percent / pyridine / CH2Cl2 / 0.5 h / 20 °C
2: 2N HCl / methanol; H2O / 7 h / Heating
3: NH4Cl / methanol; H2O / 17 h / Heating
View Scheme
2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

2-(6-Bromo-4-pyridin-2-yl-quinazolin-2-yl)-phenol
82562-62-7

2-(6-Bromo-4-pyridin-2-yl-quinazolin-2-yl)-phenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / CHCl3 / 3 h / Heating
2: 88 percent / p-toluenesulfonic acid / toluene / 5 h / Heating
View Scheme
2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

7-bromo-1,3-dihydro-3(S)-methyl-5-(pyrid-2'-yl)-2H-1,4-benzodiazepin-2-one
136295-75-5

7-bromo-1,3-dihydro-3(S)-methyl-5-(pyrid-2'-yl)-2H-1,4-benzodiazepin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.92 g / dicyclohexylcarbodiimide / CH2Cl2 / 120 h / Ambient temperature
2: 41.6 percent / H2 / 10percent Pd/C / ethanol; dioxane / 24 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: 1.92 g / dicyclohexylcarbodiimide / CH2Cl2 / 120 h / Ambient temperature
2: trifluoroacetic acid / various solvent(s) / 2.5 h / Heating
3: aq. HCl
View Scheme
2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

(S)-2-Amino-N-[4-bromo-2-(pyridine-2-carbonyl)-phenyl]-propionamide

(S)-2-Amino-N-[4-bromo-2-(pyridine-2-carbonyl)-phenyl]-propionamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.92 g / dicyclohexylcarbodiimide / CH2Cl2 / 120 h / Ambient temperature
2: trifluoroacetic acid / various solvent(s) / 2.5 h / Heating
View Scheme
2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

1,3-dihydro-3(S)-benzyl-5-(pyrid-2'-yl)-2H-1,4-benzodiazepin-2-one

1,3-dihydro-3(S)-benzyl-5-(pyrid-2'-yl)-2H-1,4-benzodiazepin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.92 g / dicyclohexylcarbodiimide / CH2Cl2 / 120 h / Ambient temperature
2: 5 percent / H2 / 10percent Pd/C / ethanol; dioxane / 24 h / Ambient temperature
View Scheme
2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

7-bromo-1,3-dihydro-3(S)-benzyl-5-(pyrid-2'-yl)-2H-1,4-benzodiazepin-2-one
136295-76-6

7-bromo-1,3-dihydro-3(S)-benzyl-5-(pyrid-2'-yl)-2H-1,4-benzodiazepin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 76.5 percent / dicyclohexylcarbodiimide / CH2Cl2 / 120 h / Ambient temperature
2: trifluoroacetic acid / various solvent(s) / 2.5 h / Heating
3: aq. HCl
View Scheme
2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

(S)-2-Amino-N-[4-bromo-2-(pyridine-2-carbonyl)-phenyl]-3-phenyl-propionamide

(S)-2-Amino-N-[4-bromo-2-(pyridine-2-carbonyl)-phenyl]-3-phenyl-propionamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76.5 percent / dicyclohexylcarbodiimide / CH2Cl2 / 120 h / Ambient temperature
2: trifluoroacetic acid / various solvent(s) / 2.5 h / Heating
View Scheme
2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

1-benzyl-7-bromo-1,3-dihydro-3(S)-benzyl-5-(pyrid-2'-yl)-2H-1,4-benzodiazepin-2-one

1-benzyl-7-bromo-1,3-dihydro-3(S)-benzyl-5-(pyrid-2'-yl)-2H-1,4-benzodiazepin-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 76.5 percent / dicyclohexylcarbodiimide / CH2Cl2 / 120 h / Ambient temperature
2: trifluoroacetic acid / various solvent(s) / 2.5 h / Heating
3: aq. HCl
4: 1) sodium methoxide, 2) sodium iodide, sodium methoxide / 1) toluene, 80 deg C, 2) a) acetonitrile, reflux, 20 h, b) 2 h
View Scheme
2-amino-5-bromobenzoyl pyridine
1563-56-0

2-amino-5-bromobenzoyl pyridine

2-(N-carbobenzoxy-S-alanyl)-amino-5-bromophenyl-pyrid-2'-yl carbinol

2-(N-carbobenzoxy-S-alanyl)-amino-5-bromophenyl-pyrid-2'-yl carbinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.92 g / dicyclohexylcarbodiimide / CH2Cl2 / 120 h / Ambient temperature
2: 11 percent / H2 / 10percent Pd/C / ethanol; dioxane / 24 h / Ambient temperature
View Scheme

1563-56-0Relevant articles and documents

Synthesis of 1,5-substituted iminodibenzo[b,f][1,5]diazocine, an analogue of Troeger's Base

Leganza, Alessandro,Bezze, Chiara,Zonta, Cristiano,Fabris, Fabrizio,De Lucchi, Ottorino,Linden, Anthony

, p. 2987 - 2990 (2006)

A method for the synthesis of 1,5-disubstituted iminodibenzo[b,f][1,5] diazocines is presented. The synthesis is achieved by the metal-free cyclization of 2-aminophenyl ketimines using the corresponding 2-aminophenyl ketone as the catalyst. The synthesis gives new insight into the mechanism of formation of this class of compounds. The presence of potential sites for hydrogen-bond formation and two aromatic bromine atoms available for functionalization make these targets attractive for further development in supramolecular chemistry. The structure of the complex derived from the iminodibenzo[b,f][1,5]diazocine and PdCl2 was determined by X-ray crystallography. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Stability indicating spectrophotometric methods for quantitative determination of bromazepam and its degradation product

A. Ali, Nesma,Abdelrahman, Maha M.,Al-Hossaini, Abdullah M.,Darwish, Hany W.,El Ghobashy, Mohamed R.,Naguib, Ibrahim A.

, (2020)

Four simple, sensitive and selective stability indicating spectrophotometric methods are presented for quantitative determination of the benzodiazepine drug; bromazepam (BMZ) and one of its reported potential impurities and degradation product; 2-(2-amino-5-bromobenzoyl) pyridine (ABP) in methanol. Method A, is isoabsorptive point coupled with D0 method, where good linearity was obtained by measuring the absorbance of BMZ at 264 nm (Aiso) in the concentration range of 2–25 μg mL?1, and the absorbance of ABP at its λmax 396 nm in concentration range of 0.5–24 μg mL?1. Method B, is ratio subtraction; the absorbance was measured at 233 nm for BMZ using 20 μg mL?1 of ABP, while ABP was determined directly at its λmax 396 nm using methanol as a solvent. Method C, was based on measuring the total peak amplitude of the first derivative of the ratio spectra (DD1) of BMZ from 301 to 326 nm using 10 μg mL?1 of ABP as a divisor and determination of ABP at peak amplitude of 293 nm using 5 μg mL?1 of BMZ as a divisor. In method D, ratio difference method, good linearity was achieved for determination of BMZ and ABP by measuring the differences between the amplitudes of ratio spectra at 312 nm and 274 nm and differences between the amplitudes of ratio spectra at 274 nm and 312 nm, respectively. The stability of BMZ was investigated under different ICH recommended forced degradation conditions. The suggested methods were then successfully applied for determination of BMZ in its pharmaceutical formulations.

Synthesis method of 2-(2-amino-5-bromobenzoyl) pyridine

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, (2020/02/19)

The invention discloses a synthesis method of 2-(2-amino-5-bromobenzoyl)pyridine. The method comprises the following processing steps: S1, reacting 4-bromo-2-bromomethylphenol, used as an initial rawmaterial, with MEMCl in an aprotic solvent to obtain 4-bromo-2-(bromomethyl)-1-((2-methoxyethoxy)methoxy)benzene; S2, reacting the 4-bromo-2-(bromomethyl)-1-((2-methoxyethoxy)methoxy)benzene with trimethyl borate under the action of a catalyst to prepare a boric acid compound (5-bromo-2-(((2-methoxyethoxy)methoxy)benzyl) boric acid; and S3, adding 2-bromopyridine and [1,1'-bis(diphenylphosphino)ferrocene]-palladium dichloride into the (5-bromo-2-(((2-methoxyethoxy)methoxy)benzyl)boric acid in order to prepare 2-(5-bromo-2-(((2-methoxyethoxy)methoxy)benzyl)pyridine. The method has the advantages of high atom utilization rate, environmental friendliness due to the recoverable solvent, high yield, convenience in operation, and suitableness for industrial production.

Preparation method of benzodiazepine derivatives

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Paragraph 0050-0051; 0075; 0076; 0077-0079, (2018/07/30)

The invention relates to a preparation method of benzodiazepine derivatives. The preparation method comprises preparing a compound shown in the formula (III) from a compound shown in the formula (V),preparing a compound shown in the formula (II) through a reaction and finally preparing benzodiazepine derivatives shown in the formula (I) and their pharmaceutically acceptable salts. The invention also discloses an intermediate in the preparation process and a preparation method thereof. The preparation method shortens the reaction processes, improves the reaction yield, is simple, is easy to operate and control and is conducive to expanded production.

DIHYDROQUINAZOLINONE ANALOGUES AS BRD4 INHIBITORS

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Page/Page column 62, (2014/10/15)

The present invention encompasses compounds of general formula (I) wherein the groups R1 to R4 and A1 to A5 have the meanings given in the claims and in the specification. The compounds of the invention are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation pharmaceutical preparations containing such compounds and their uses as a medicament.

DIHYDROQUINAZOLINONE ANALOGUES

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Paragraph 0303-0306, (2014/10/16)

The present invention encompasses compounds of general formula (I) wherein the groups R1 to R4 and A1 to A5 have the meanings given in the claims and in the specification. The compounds of the invention are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation pharmaceutical preparations containing such compounds and their uses as a medicament.

Stereospecific anxiolytic and anticonvulsant agents with reduced muscle-relaxant, sedative-hypnotic and ataxic effects

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Page/Page column 60-61, (2008/06/13)

The present invention provides compositions and methods of using stereospecific benzodiazepine derivatives, their salts and prodrugs for the treatment of anxiolytic or convulsant disorders having the side effects of reduced alcohol craving in human alcoholics and a concomitant reduced sedative, hypnotic, muscle relaxant and ataxic side-effects. The invention further provides pharmaceutical compositions for treatment of anxiolytic and convulsant disorders in subjects in need thereof, comprising a compound, prodrug or a salt having a chemical structure represented by any one of Formula I-XXI and a pharmaceutically-acceptable carrier.

SHORT-ACTING BENZODIAZEPINES

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Page/Page column 11, (2008/06/13)

It has now been found that compounds of the present invention as described in Benzodiazepine derivatives of Formula (I) containing a carboxylic ester moiety and thereby capable of being inactivated by nonspecific tissue esterases in an organ-independent elimination mechanism and thereby providing a more predictable and reproducible pharmacodynamic profile. The compounds of the present invention are suitable for therapeutic purposes, including sedative-hypnotic, anxiolytic, muscle relaxant and anticonvulsant purposes and are useful to be administered intravenously in the following clinical settings: preoperative sedation, anxiolysis, and amnestic use for perioperative events; conscious sedation during short diagnostic, operative or endoscopic procedures; as a component for the induction and maintenance of general anesthesia, prior and/or concomitant to the administration of other anesthetic agents; ICU sedation.

Kinetics of the acid hydrolysis of diazepam, bromazepam, and flunitrazepam in aqueous and micellar systems

Moro,Novillo-Fertrell,Velazquez,Rodriguez

, p. 459 - 468 (2007/10/02)

A kinetic study of the acid hydrolysis of aqueous diazepam, bromazepam, and flunitrazepam was carried out at 25 °C using a spectrophotometric method. For diazepam and flunitrazepam, the experimental pseudo first-order rate constant decreased as the acid concentration was increased. The contrary behavior was found in the case of bromazepam. A kinetic scheme that includes the hydrolysis reaction of both protonated and nonprotonated species of the drug can account for these results. Also, the kinetics of the acid hydrolysis of the same drugs in the presence of micellar aggregates [nonionic polyoxyethylene-23-dodecanol (Brij 35); cationic cetyl trymethyl ammonium bromide (CTAB); and anionic sodium decyl (SdeS), dodecyl (SDS), and tetradecyl (STS) sulfate] was studied at 25 °C. Negligible effects were observed in the cases of nonionic and cationic micelles. Anionic micelles produced an inhibitory effect in the reaction velocity. This effect increased as the hydrophobic nature of the surfactant increased. All these facts are interpreted quantitatively by means of a pseudophase model.

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