ChemicalBook CAS DataBase List Mirabegron

Mirabegron synthesis

2synthesis methods

Product Name:Mirabegron
CAS Number:223673-61-8
Molecular formula:C21H24N4O2S
Molecular Weight:396.51

Mirabegron (formerly YM-178, trade name Myrbetriq) is a drug for the treatment of overactive bladder. It was developed by Astellas Pharma and was approved in the United States in July 2012. Mirabegron activates the β3 adrenergic receptor in the detrusor muscle in the bladder, which leads to muscle relaxation and an increase in bladder capacity.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

ROUTE 8

ROUTE 9

Vedantham, Ravindra; Kandagatla, Bhaskar; Vyala, Sunitha; Raju, V. V. N. K. V. Prasada; Cherukupalli, Praveen; Iqbal, Javed; Dahanukar, Vilas H.; Kagga, Mukkanti; Bandichhor, Rakeshwar; Oruganti, Srinivas. Practical synthesis of Mirabegron. Journal of Chemical and Pharmaceutical Research. Volume 7. Issue 4. Pages 1473-1478. Journal; Online Computer File. (2015).

29676-71-9 Synthesis

29676-71-9
454 suppliers
$13.00/5g

521284-22-0 Synthesis

(alphaR)-alpha-[[[2-(4-Aminophenyl)ethyl]amino]methyl]benzenemethanol hydrochloride

521284-22-0
195 suppliers
$10.00/250mg

223673-61-8
475 suppliers
$5.00/1mg

Yield:223673-61-8 84.5%

Reaction Conditions:

with hydrogenchloride;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in water at 28; for 3 h;Concentration;

Steps:

1d Example idStep d: Preparation of a-form of crystalline (R)-2-(2-aminothiazol-4-yl)-4 ‘-12- F(2-hydroxy- 2-phenylethylaminol -ethyll -acetanilide (Mirabepron)
To a mixed solution of (100 g) (R)-2-[[2-(4-aminophenyl)ethyl]-amino]-l-phenylethanolmonohydrochioride (prepared according to example Ic), 2-aminothiazole-4-yl-acetic acid (55.10 g), concentrated hydrochloric acid (35.61 g) and water (1500 mL); 1-(3-dimethylaminopropyl)-3- ethylcarbodiimide monohydrchloride (EDC.HCI) (72.01 g) was added at 28°C (±2) and the mixture was stirred for 1 hr. l-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochioride (EDC.HCI) (7.2 g) was added into the mixture at 28°C (±2) and the mixture was stirred for 2 hrs. The reaction mass was washed with mixture of ethyl acetate (400 mL) and n-butanol (100 mL). To the reaction mixture, n-butariol (1000 mL) was added followed by addition of aqueous solution of ammonia (20%, 80 mL). The organic layer was separated and successively washed with aqueous ammonia (5%, 1000 mE) and then followed by water. The organic layer was partially concentrated under vacuo and the temperature was raised to 68°C (±2). To this solution, toluene (1400 mE) was added and gradually cooled to room temperature. The solid obtained was filtered, washed with toluene and dried under vacuo at 48°C (±2) to obtain crystals of CL form of Mirabegron having PXRD pattern shown in Fig. 1 and Infrared spectrum (IR) show in Fig 2.Yield: 114.1 g (84.5%); Purity by HPLC: 99.80%.

References:

MEGAFINE PHARMA (P) LTD.;MATHAD, Vijayavitthal Thippannachar;DESHMUKH, Dattatray Gulabrao;VARPE, Sagar Popat;NAVALE, Pravin Mahadu WO2015/44965, 2015, A1 Location in patent:Page/Page column 34; 36

FullText

29676-71-9 Synthesis

29676-71-9
454 suppliers
$13.00/5g

BenzeneMethanol, a-[[[2-(4-aMinophenyl)ethyl]aMino]Methyl]-, (aR)-

391901-45-4
102 suppliers
$13.00/1g

223673-61-8
475 suppliers
$5.00/1mg

References

Mirabegron Related Search:

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Mirabegron synthesis

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