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1187594-09-7

Basic Information
CAS No.: 1187594-09-7
Name: Baricitinib
Article Data: 14
Molecular Structure:
Molecular Structure of 1187594-09-7 (Baricitinib)
Formula: C16H17N7O2S
Molecular Weight: 371.423
Synonyms: INCB 028050;LY 3009104;1-(Ethylsulfonyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]-3-azetidineacetonitrile;
EINECS: 691-421-4
Density: 1.6±0.1 g/cm3
PSA: 128.94000
LogP: 2.11438
Synthetic route

2-(1-(ethanesulfonyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)azetidine-3-yl)acetonitrile

3680-69-1

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

1187594-09-7

Baricitinib

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80 - 85℃; for 5h;99%
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In water; toluene; tert-butyl alcohol at 100℃; for 48h; Concentration; Temperature; Solvent; Reagent/catalyst; Suzuki Coupling; Inert atmosphere;90%
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In tetrahydrofuran; water at 90℃; for 19h; Autoclave; Inert atmosphere;90%
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In water; toluene; tert-butyl alcohol for 48h; Suzuki Coupling; Reflux; Inert atmosphere;84%

tert-butyl 4-{1-[3-(cyanomethyl)-1-(ethylsulfonyl)azetidin-3-yl]-1H-pyrazol-4-yl}-7H-pyrrolo[2.3-d]pyrimidine-7-carboxylate

1187594-09-7

Baricitinib

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 40 - 45℃;93%
With hydrogenchloride In ethanol at 40 - 45℃;93%
In water; butan-1-ol at 90℃;92.7%
1187595-85-2

2-[1-(ethanesulfonyl)azetidin-3-ylidene]acetonitrile

C14H15N5O2

1187594-09-7

Baricitinib

Conditions
ConditionsYield
Stage #1: C14H15N5O2 With potassium carbonate In acetonitrile at 20℃; for 0.5h;
Stage #2: 2-[1-(ethanesulfonyl)azetidin-3-ylidene]acetonitrile With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 40℃; for 8h;
91.2%
1187595-90-9

(4-{1-[3-(cyanomethyl)-1-(ethylsulphonyl)azetidin-3-yl]-1H-pyrazol-4-yl}-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl 2,2-dimethylpropanoate

1187594-09-7

Baricitinib

Conditions
ConditionsYield
Stage #1: (4-{1-[3-(cyanomethyl)-1-(ethylsulphonyl)azetidin-3-yl]-1H-pyrazol-4-yl}-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl 2,2-dimethylpropanoate With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 2 - 3h;
Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water at 20℃; for 0.5h; pH=7 - 7.5; Product distribution / selectivity;
86%
With sodium hydroxide In tetrahydrofuran; methanol at 20 - 25℃; for 3h;81%
With sodium hydroxide In tetrahydrofuran; methanol; water at 20 - 30℃;
1187594-13-3

2-(1-(ethylsulfonyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile

1187594-09-7

Baricitinib

Conditions
ConditionsYield
Stage #1: 2-[1-ethanesulfonyl-3-[4-(7-[(2-(trimethylsilyl)ethoxy)methyl]-7H-pyrrolo[2,3-d]pyrimidine-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl]acetonitrile With lithium tetrafluoroborate; water In acetonitrile at 75℃;
Stage #2: With ammonium hydroxide; water In acetonitrile at 0 - 10℃; pH=9 - 10; Product distribution / selectivity;
83.8%

2-(1-(ethylsulfonyl)-3-(4-(7-p-tolylsulfonyl-7H-pyrrolo[2,3-d]pyrimidine-4-yl)-1H-pyrazol-1-yl)-3-azetidin-3-yl)acetonitrile

1187594-09-7

Baricitinib

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 50 - 55℃;83%

2-(1-(ethylsulfonyl)-3-(4-(7-phenylsulfonyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile

1187594-09-7

Baricitinib

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In 2-methyltetrahydrofuran Reflux;81.2%

C12H16BN3O2

2-(3-(4-bromo-1H-pyrazol-1-yl)-1-(ethylsulfonyl)azetidin-3-yl)acetonitrile

1187594-09-7

Baricitinib

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In water; N,N-dimethyl-formamide at 85 - 90℃; Inert atmosphere;76%

2-(3-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-pyrazole-1-yl)-1-(ethylsulfonyl)azetidin-3-yl)acetonitrile

3680-69-1

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

1187594-09-7

Baricitinib

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl acetamide; water at 95 - 100℃; Inert atmosphere;73%

2-(3-(4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile dihydrochloride salt

594-44-5

Ethanesulfonyl chloride

1187594-09-7

Baricitinib

Conditions
ConditionsYield
Stage #1: 2-(3-(4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile dihydrochloride salt; Ethanesulfonyl chloride With N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 5℃; for 6h;
Stage #2: With ammonium hydroxide In acetonitrile at 20℃; for 4h;
65%
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    Product Name: Baricitinib Synonyms: aricitinib (LY3009104, INCB028050);Baricitinib Chemical Structure;Barrickini;1-(Ethylsulfonyl)-3-[4-(7H-pyrrolo[2,3-d]pyriMidin-4-yl)-1H-pyrazol-1-yl]-3-azetidineacetonitrile;Baricitinib;INCB 028050;LY 3009104;B

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Specification

The Baricitinib, with the CAS registry number 1187594-09-7, is also known as 3-Azetidineacetonitrile, 1-(ethylsulfonyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]-. This chemical's molecular formula is C16H17N7O2S and molecular weight is 371.42. What's more, its systematic name is {1-(Ethylsulfonyl)-3-[4-(1H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]-3-azetidinyl}acetonitrile. This chemical is an oral JAK1 and JAK2 inhibitor. It has shown encouraging results in a clinical trial for rheumatoid arthritis.

Physical properties of Baricitinib are: (1)ACD/LogP: -0.06±0.73; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.07; (4)ACD/LogD (pH 7.4): -0.07; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 21.62; (8)ACD/KOC (pH 7.4): 21.97; (9)#H bond acceptors: 9; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 128.94 Å2; (13)Index of Refraction: 1.763; (14)Molar Refractivity: 98.2±0.5 cm3; (15)Molar Volume: 238.1±7.0 cm3; (16)Polarizability: 38.9±0.5×10-24cm3; (17)Surface Tension: 73.0±7.0 dyne/cm; (18)Density: 1.6±0.1 g/cm3.

You can still convert the following datas into molecular structure:
(1)SMILES: CCS(=O)(=O)N1CC(C1)(CC#N)n2cc(cn2)c3c4cc[nH]c4ncn3
(2)Std. InChI: InChI=1S/C16H17N7O2S/c1-2-26(24,25)22-9-16(10-22,4-5-17)23-8-12(7-21-23)14-13-3-6-18-15(13)20-11-19-14/h3,6-8,11H,2,4,9-10H2,1H3,(H,18,19,20)
(3)Std. InChIKey: XUZMWHLSFXCVMG-UHFFFAOYSA-N