Product Name

  • Name

    Anagrelide hydrochloride

  • EINECS 680-360-9
  • CAS No. 58579-51-4
  • Article Data7
  • CAS DataBase
  • Density 1.77g/cm3
  • Solubility
  • Melting Point >280 °C
  • Formula C10H8Cl3N3O
  • Boiling Point 376.5 °C at 760 mmHg
  • Molecular Weight 292.552
  • Flash Point 181.5 °C
  • Transport Information
  • Appearance Off-white powder
  • Safety 26
  • Risk Codes 22-36/37/38
  • Molecular Structure Molecular Structure of 58579-51-4 (Anagrelide hydrochloride)
  • Hazard Symbols Xn
  • Synonyms Imidazo[2,1-b]quinazolin-2(3H)-one,6,7-dichloro-1,5-dihydro-, monohydrochloride (9CI);6,7-Dichloro-1,5-dihydroimidazo[2,1-b]quinazolin-2(3H)-one Hydrochloride;Agrelin;Agrylin;BL 4162A;BMY 26538-01;
  • PSA 44.70000
  • LogP 2.43060

Synthetic route

anagrelide hemiformate

anagrelide hemiformate

anagrelide hydrochloride
58579-51-4

anagrelide hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water; toluene at 24 - 38℃; for 1.35h; Concentration; Temperature; Time;97%
ethyl 2,5,6-trichloro-3,4-dihydroquinazoline-3-acetate
78052-19-4

ethyl 2,5,6-trichloro-3,4-dihydroquinazoline-3-acetate

anagrelide hydrochloride
58579-51-4

anagrelide hydrochloride

Conditions
ConditionsYield
With ammonium hydroxide In ethanol at 120℃; for 16h; sealed tube;78%
anagrelide
68475-42-3

anagrelide

anagrelide hydrochloride
58579-51-4

anagrelide hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol for 0.166667h; Heating / reflux;70%
With hydrogenchloride In dimethyl sulfoxide at 50℃;44.2%
With hydrogenchloride In ethanol; water at 78 - 80℃; for 0.133333h;
2,5,6-Trichloro-3,4-dihydro-quinazoline
78052-12-7

2,5,6-Trichloro-3,4-dihydro-quinazoline

anagrelide hydrochloride
58579-51-4

anagrelide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / K2CO3 / butan-2-one / Heating
2: 78 percent / 10percent ammonia / ethanol / 16 h / 120 °C / sealed tube
View Scheme
2,4,5,6-tetrachloroquinazoline
78052-21-8

2,4,5,6-tetrachloroquinazoline

anagrelide hydrochloride
58579-51-4

anagrelide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 94 percent / NaBH4 / CHCl3; ethanol / 2 h / 25 °C
2: 76 percent / K2CO3 / butan-2-one / Heating
3: 78 percent / 10percent ammonia / ethanol / 16 h / 120 °C / sealed tube
View Scheme
(2-amino-5,6-dichloroquinazolin-3(4H)-yl)acetic acid methyl ester hydrochloride

(2-amino-5,6-dichloroquinazolin-3(4H)-yl)acetic acid methyl ester hydrochloride

anagrelide hydrochloride
58579-51-4

anagrelide hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water at 37℃; for 1h;
bromocyane
506-68-3

bromocyane

N-(6-amino-2,3-dichlorobenzyl)glycine ethyl ester
70406-92-7

N-(6-amino-2,3-dichlorobenzyl)glycine ethyl ester

anagrelide hydrochloride
58579-51-4

anagrelide hydrochloride

Conditions
ConditionsYield
In 2-methoxy-ethanol
4,5-Dichloro-1H-indole-2,3-dione
1677-47-0

4,5-Dichloro-1H-indole-2,3-dione

anagrelide hydrochloride
58579-51-4

anagrelide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
2: hydrogenchloride; borane / tetrahydrofuran
3: hydrogenchloride; thionyl chloride; triethylamine / benzene
4: 2-methoxy-ethanol
View Scheme
6-amino-2,3-dichlorobenzoic acid
20776-60-7

6-amino-2,3-dichlorobenzoic acid

anagrelide hydrochloride
58579-51-4

anagrelide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride; borane / tetrahydrofuran
2: hydrogenchloride; thionyl chloride; triethylamine / benzene
3: 2-methoxy-ethanol
View Scheme
3,4-dichloro-2-hydroxymethylaniline
70380-51-7

3,4-dichloro-2-hydroxymethylaniline

anagrelide hydrochloride
58579-51-4

anagrelide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride; thionyl chloride; triethylamine / benzene
2: 2-methoxy-ethanol
View Scheme
methanol
67-56-1

methanol

methyl bisulfate
75-93-4

methyl bisulfate

anagrelide hydrochloride
58579-51-4

anagrelide hydrochloride

C11H11Cl2N3O2*CH4O4S

C11H11Cl2N3O2*CH4O4S

Conditions
ConditionsYield
Stage #1: methanol; anagrelide hydrochloride With sulfuric acid at 0 - 85℃; for 21h;
Stage #2: methyl bisulfate Temperature; Reagent/catalyst;		86.8%
...Expand
ethanol
64-17-5

ethanol

anagrelide hydrochloride
58579-51-4

anagrelide hydrochloride

ethyl (2‑amino‑5,6‑dichloroquinazoline‑3(4H)‑yl)acetate

ethyl (2‑amino‑5,6‑dichloroquinazoline‑3(4H)‑yl)acetate

Conditions
ConditionsYield
With sulfuric acid at 85℃; for 20h; Temperature; Reagent/catalyst;83.4%
formic acid
64-18-6

formic acid

anagrelide hydrochloride
58579-51-4

anagrelide hydrochloride

anagrelide hemiformate

anagrelide hemiformate

Conditions
ConditionsYield
at 40℃;5.83 g

Anagrelide hydrochloride Chemical Properties

Molecular Structure of Imidazo[2,1-b]quinazolin-2(3H)-one,6,7-dichloro-1,5-dihydro-, hydrochloride (1:1) (CAS NO.58579-51-4):

IUPAC Name: 6,7-Dichloro-5,10-dihydro-3H-imidazo[2,1-b]quinazolin-2-one hydrochloride
Canonical SMILES: C1C2=C(C=CC(=C2Cl)Cl)NC3=NC(=O)CN31.Cl
InChI: InChI=1S/C10H7Cl2N3O.ClH/c11-6-1-2-7-5(9(6)12)3-15-4-8(16)14-10(15)13-7; /h1-2H,3-4H2,(H,13,14,16); 1H
InChIKey: TVWRQCIPWUCNMI-UHFFFAOYSA-N
Molecular Weight: 292.54902 [g/mol]
Molecular Formula: C10H8Cl3N3O
H-Bond Donor: 2
H-Bond Acceptor: 3 
Density: 1.77g/cm3
Flash Point: 181.5 °C
Enthalpy of Vaporization: 62.42 kJ/mol
Boiling Point: 376.5 °C at 760 mmHg
Vapour Pressure: 7.21E-06 mmHg at 25 °C
Appearance: Off-White Powder
Melting Point: >280 °C
Solubility: Soluble to 10 mM in DMSO,soluble in water
Classification Code:  Antithrombotic; Drug / Therapeutic Agent; Fibrinolytic Agents; Platelet Aggregation Inhibitors 
Product Categories: Intermediates & Fine Chemicals; Pharmaceuticals

Anagrelide hydrochloride Uses

 Imidazo[2,1-b]quinazolin-2(3H)-one,6,7-dichloro-1,5-dihydro-, hydrochloride (1:1) (CAS NO.58579-51-4) is used as an antithrombocythemic.

Anagrelide hydrochloride Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
monkey LD50 oral > 200mg/kg (200mg/kg)   New Drugs Annual: Cardiovascular Drugs. Vol. 1, Pg. 277, 1983.
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   New Drugs Annual: Cardiovascular Drugs. Vol. 1, Pg. 277, 1983.
mouse LD50 oral > 2500mg/kg (2500mg/kg)   New Drugs Annual: Cardiovascular Drugs. Vol. 1, Pg. 277, 1983.
rat LD50 oral > 1500mg/kg (1500mg/kg)   New Drugs Annual: Cardiovascular Drugs. Vol. 1, Pg. 277, 1983.

Anagrelide hydrochloride Specification

 Imidazo[2,1-b]quinazolin-2(3H)-one,6,7-dichloro-1,5-dihydro-, hydrochloride (1:1) (CAS NO.58579-51-4), its Synonyms are 6,7-Dichloro-1,5-dihydroimidazo(2,1-b)-quinazolin-2(3H)-one monohydrochloride ; Agrelin ; Agrylin ; Anagrelid hydrochlorid ; Anagrelide HCl ; Anagrelide hydrochloride ; Imidazo(2,1-b)quinazolin-2(3H)-one, 6,7-dichloro-1,5-dihydro-, monohydrochloride .

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