[ CAS No. 1050501-88-6 ] {[proInfo.proName]}

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Quality Control of [ 1050501-88-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1050501-88-6 ]

SDS Specification

Alternatived Products of [ 1050501-88-6 ]

Product Details of [ 1050501-88-6 ]

CAS No. :	1050501-88-6	MDL No. :	MFCD11504927
Formula :	C₅H₄BrClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OPKKXWUGXHSFQI-UHFFFAOYSA-N
M.W :	207.46	Pubchem ID :	45480430
Synonyms :

Calculated chemistry of [ 1050501-88-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.35
TPSA :	38.91 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.6
Log Po/w (XLOGP3) :	2.16
Log Po/w (WLOGP) :	2.09
Log Po/w (MLOGP) :	1.19
Log Po/w (SILICOS-IT) :	2.03
Consensus Log Po/w :	1.81

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.98
Solubility :	0.217 mg/ml ; 0.00105 mol/l
Class :	Soluble
Log S (Ali) :	-2.61
Solubility :	0.51 mg/ml ; 0.00246 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.14
Solubility :	0.15 mg/ml ; 0.000724 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.11

Safety of [ 1050501-88-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1050501-88-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1050501-88-6 ]

[ 1050501-88-6 ] Synthesis Path-Downstream 1~16

1
[ 1050501-88-6 ]
[ 1352200-87-3 ]

Reference： [1]Patent: US2011/306589,2011,A1
[2]Patent: WO2011/154327,2011,A1

2
[ 1050501-88-6 ]
[ 1352200-88-4 ]

Reference： [1]Patent: US2011/306589,2011,A1
[2]Patent: WO2011/154327,2011,A1

3
[ 64-17-5 ]
[ 201230-82-2 ]
[ 1050501-88-6 ]
[ 1352200-86-2 ]

Yield	Reaction Conditions	Operation in experiment
30%	With triethylamine;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In toluene; at 80℃; under 37503.8 Torr; for 16h;Inert atmosphere; autoclave;	A solution of <strong>[1050501-88-6]2-bromo-6-chloro-pyridin-3-ylamine</strong> (1.0 g, 4.8 mmol) in ethanol (15 ml) and toluene (15 ml) was charged under argon atmosphere with (1,1'-bis(diphenylphosphino)-ferrocene)palladium(II) dichloride complex with dichloromethane (200 mg ; 0.245 mmol) and triethylamine (1.67 ml, 12.1 mmol) in an autoclave, was flushed with carbon monoxide (3 times, 20 bar) and stirred at 80 C. under carbon monoxide atmosphere (50 bar) for 16 h. Upon cooling to ambient temperature and pressure release, the reaction mixture was filtrated and the solvents were removed. The product was obtained after purification by silica gel chromatography using a dichloromethane /methanol /ammonia gradient and recrystallisation from dichloromethane as light yellow solid (290 mg, 30%).
30%	With triethylamine;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In toluene; at 80℃; under 15001.5 - 37503.8 Torr; for 16h;Inert atmosphere; autoclave;	A solution of <strong>[1050501-88-6]2-bromo-6-chloro-pyridin-3-ylamine</strong> (1.0 g, 4.8 mmol) in ethanol (15 ml) and toluene (15 ml) was charged under argon atmosphere with (l,l'-bis(diphenylphosphino)- ferrocene)palladium(II) dichloride complex with dichloromethane (200 mg; 0.245 mmol) and triethylamine (1.67 ml, 12.1 mmol) in an autoclave, was flushed with carbon monoxide (3 times, 20 bar) and stirred at 80 C under carbon monoxide atmosphere (50 bar) for 16 h. Upon cooling to ambient temperature and pressure release, the reaction mixture was filtrated and the solvents were removed. The product was obtained after purification by silica gel chromatography using a dichloromethane/methanol/ammonia gradient and recrystallisation from dichloromethane as light yellow solid (290 mg, 30%).

Reference： [1]Patent: US2011/306589,2011,A1 .Location in patent: Page/Page column 91-92
[2]Patent: WO2011/154327,2011,A1 .Location in patent: Page/Page column 223

4
[ 1050501-88-6 ]
[ 127-17-3 ]
[ 800401-63-2 ]

Yield	Reaction Conditions	Operation in experiment
82.6%	With palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 100℃;	Step 2: synthesis of 5-chloro-lH-pyrrolo[3,2-b]pyridine-2-carboxylic acid 11-b2-oxopropanoic acid (36.22 g, 411.31 mmol), palladium(II)acetate (7.74 g, 34.15 mmol) and Et3N (69.11 g, 682.94 mmol) were added to a solution of 2-bromo-6- chloropyridin-3 -amine 11-a (32.20 g, 155.21 mmol) and TPP (35.83 g, 136.59 mmol) in dry DMF (300 ml). The reaction mixture was stirred at 100C overnight. The solvent was then evaporated, water was added and the water layer was washed with EtOAc. The water layer was acidified with cone. HCl. The precipitate was filtered off and dried, yielding 25.21 g of the wanted product 11-b (82.6 %). m/z = 197.1 (M+H)+, CI pattern.
82.6%	With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃;	2-oxopropanoic acid (36.22 g, 411.31 mmol), palladium(II)acetate (7.74 g, 34.15 mmol) and Et3N (69.11 g, 682.94 mmol) were added to a solution of 2-bromo-6- chloropyridin-3-amine 28-b (32.20 g, 155.21 mmol) and TPP (35.83 g, 136.59 mmol) in dry DMF (300 ml). The reaction mixture was stirred at 100C overnight. The solvent was then evaporated, water was added and the water layer was washed with EtOAc. The water layer was acidified with cone. HC1. The precipitate was filtered off and dried, yielding 25.21 g of the intermediate 28-c (82.6 %)
82.6%	With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃;	2-oxopropanoic acid (36.22 g, 411.31 mmol), palladium(II)acetate (7.74 g,34.15 mmol) and Et3N (69.11 g, 682.94 mmol) were added to a solution of<strong>[1050501-88-6]2-bromo-6-chloropyridin-3-amine</strong> 49-a (32.20 g, 155.21 mmol) and TPP (35.83 g, 136.59 mmol)in dry DMF (300 ml). The reaction mixture was stirred at 100C overnight. The solvent was then evaporated, water was added and the water layer was washed withEtOAc. The water layer was acidified with cone. HCl. The precipitate was filtered offand dried, yielding 25.21 g of the wanted product 49-b (82.6 %).m/z = 197.1 (M+It.

82.6%	With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃;	Step 2: synthesis of 5-chloro-1H-pyrrolo[3,2-bjpyridine-2-carboxylic acid (intermediate 20b)2-oxopropanoic acid (36.22 g, 411.31 mmol), palladium(II)acetate (7.74 g, 34.15 mmol) and Et3N (69.11 g, 682.94 mmol) were added to a solution of 2-bromo-6- chloropyridin-3-amine 20a (32.20 g, 155.21 mmol) and TPP (35.83 g, 136.59 mmol) in dry DMF (300 ml). The reaction mixture was stirred at 100C overnight. The solvent was then evaporated, water was added and the water layer was washed with EtOAc.The water layer was acidified with conc. HC1. The precipitate was filtered off and dried, yielding 25.21 g of the wanted product 20b (82.6 %). m/z = 197.1 (M+H), Cl pattern.
82.6%	With palladium diacetate; triethylamine; triphenylphosphine; In water; N,N-dimethyl-formamide; at 100℃;	2-oxopropanoic acid (36.22 g, 411.31 mmol), palladium(II)acetate (7.74 g, 34.15 mmol) and Et3N (69.11 g, 682.94 mmol) were added to a solution of <strong>[1050501-88-6]2-bromo-6-chloropyridin-3-amine</strong> 49-a (32.20 g, 155.21 mmol) and TPP (35.83 g, 136.59 mmol) in dry DMF (300 ml). The reaction mixture was stirred at 100 C. overnight. The solvent was then evaporated, water was added and the water layer was washed with EtOAc. The water layer was acidified with conc. HCl. The precipitate was filtered off and dried, yielding 25.21 g of the wanted product 49-b (82.6%). m/z=197.1 (M+1)+.
	With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 115℃; for 18h;Inert atmosphere;	To the mixture of <strong>[1050501-88-6]2-bromo-6-chloropyridin-3-amine</strong> (5 g, 24.4 mmol), Pd(OAc)2 (1.09 g, 4.88 mmol), PPh3 (1.91 g, 7.32 mmol) and triethylamine (10.8 g, 107.3 mmol) in DMF (30 mL) in N2 atmosphere, was added 2-oxopropanoic acid (5.69 g, 64.6 mmol) by a syringe. The resulting mixture was heated at 115C for l8hrs under N2. The reaction mixture was cooled to room temperature and poured into water (200 mL) The resulting precipitate was filtered and the filtrate was washed with EA(30 mL x 3). The pH of aqueous phase was adjusted with iN aq. HC1 solution to pH 4, and the resulting precipitate was collected by filtration and dried by reduced pressure to give 5-chloro-1H-pyrrolo[3,2-bjpyridine-2- carboxylic acid (2.44 g, 51%) as a solid. HPLC/UV purity: 90%; LC-MS (ESI): 197.1 (M + 1).

Reference： [1]Patent: WO2012/80450,2012,A1 .Location in patent: Page/Page column 26
[2]Patent: WO2013/186335,2013,A1 .Location in patent: Page/Page column 87; 88
[3]Patent: WO2013/186333,2013,A1 .Location in patent: Page/Page column 102; 103
[4]Patent: WO2014/60411,2014,A1 .Location in patent: Page/Page column 56
[5]Patent: US2015/111868,2015,A1 .Location in patent: Paragraph 0858; 0859
[6]Patent: WO2018/204176,2018,A1 .Location in patent: Paragraph 00472

5
[ 5350-93-6 ]
[ 1050501-88-6 ]

Yield	Reaction Conditions	Operation in experiment
99.8%		Step 1: synthesis of 2-bromo-6-chloropyridin-3-amine 11-aBromine (24.86 g, 155.57 mmol) was added to a solution of 6-chloropyridin-3 -amine (20.00 g, 155.57 mmol) and sodium acetate (25.52 g, 311.14 mmol) in acetic acid (383 ml). The reaction mixture was stirred at room temperature for 1 hour. Acetic acid was then evaporated. The residue was dissolved in EtOAc, washed with saturated aqueous Na2C03, water and brine. The organic layer was dried over MgS04, filtered and evaporated, yielding 32.20 g of the desired product 11-a (99.8%). m/z = 206.96 (M+H)+, Cl+Br pattern.
99.8%	With bromine; sodium acetate; acetic acid; at 20℃; for 1h;	Bromine (24.86 g, 155.57 mmol) was added to a solution of 6-chloropyridin-3 -amine 28-a (20.00 g, 155.57 mmol) and sodium acetate (25.52 g, 311.14 mmol) in acetic acid (383 ml). The reaction mixture was stirred at room temperature for 1 hour. Acetic acid was then evaporated. The residue was dissolved in EtOAc, washed with saturated aqueous Na2C03, water and brine. The organic layer was dried over MgSC^, filtered and evaporated, yielding 32.20 g of the desired intermediate 28-b (99.8%).
99.8%	With bromine; sodium acetate; acetic acid; at 20℃; for 1h;	Bromine (24.86 g, 155.57 mmol) was added to a solution of6-chloropyridin-3-amine (20.00 g, 155.57 mmol) and sodium acetate (25.52 g, 311.14 mmol) in acetic acid(383 ml). The reaction mixture was stirred at room temperature for 1 hour. Acetic acidwas then evaporated. The residue was dissolved in EtOAc, washed with saturatedaqueous Na2C03, water and brine. The organic layer was dried over MgS04, filteredand evaporated, yielding 32.20 g of the desired product 49-a (99.8%). m/z = 206.96 (M+ It

99.8%	With bromine; sodium acetate; acetic acid; at 25℃; for 1h;	Step 1: synthesis of 2-bromo-6-chloropyridin-3-amine (intermediate 20a)Bromine (24.86 g, 155.57 mmol) was added to a solution of 6-chloropyridin-3-amine(20.00 g, 155.57 mmol) and sodium acetate (25.52 g, 311.14 mmol) in acetic acid(383 ml). The reaction mixture was stirred at room temperature for 1 hour. Acetic acidwas then evaporated. The residue was dissolved in EtOAc, washed with saturatedaqueous Na2CO3, water and brine. The organic layer was dried over MgSO4, filteredand evaporated, yielding 32.20 g of the desired product 20a (99.8%). m/z = 206.96 (M+H), Cl+Br pattern.
99.8%	With bromine; sodium acetate; acetic acid; In ethyl acetate; at 20℃; for 1h;	Bromine (24.86 g, 155.57 mmol) was added to a solution of 6-chloropyridin-3-amine (20.00 g, 155.57 mmol) and sodium acetate (25.52 g, 311.14 mmol) in acetic acid (383 ml). The reaction mixture was stirred at room temperature for 1 hour. Acetic acid was then evaporated. The residue was dissolved in EtOAc, washed with saturated aqueous Na2CO3, water and brine. The organic layer was dried over MgSO4, filtered and evaporated, yielding 32.20 g of the desired product 49-a (99.8%). m/z=206.96 (M+1)+
	With bromine; sodium acetate; acetic acid; at 20℃; for 18h;	To a mixture of 6-chloropyridin-3-amine (5 g, 38.9 mmol) and NaOAc (6.37 g, 77.8 mmol) in AcOH (30 mL) was added a solution of bromine (6.8 g, 42.8 mmol) in AcOH(5 mL) . The resulting reaction mixture was stirred at room temperature for 1 8hrs. Acetic acid was removed under reduced pressure to give the residue, which was dissolved into EA (50 mL), washed by NaHCO3 aqueous (20 mL x 5), water and brine. The organic layers was dried over Na2SO4, and the drying agent was filtered off. The filtrate was concentrated in vavuo to give the crude product, which was purified by silica gel chromatography (silica gel, eluting with 5% methanol in DCM) to give (5 g, 62%) as an orange solid. HPLC/UV purity: 90%; LC-MS (ESI): 207.3 (M + 1).

Reference： [1]Patent: WO2012/80450,2012,A1 .Location in patent: Page/Page column 25
[2]Patent: WO2013/186335,2013,A1 .Location in patent: Page/Page column 87
[3]Patent: WO2013/186333,2013,A1 .Location in patent: Page/Page column 102
[4]Patent: WO2014/60411,2014,A1 .Location in patent: Page/Page column 56
[5]Patent: US2015/111868,2015,A1 .Location in patent: Paragraph 0856; 0857
[6]Organic Process Research and Development,2012,vol. 16,p. 1069 - 1081
[7]Patent: WO2018/204176,2018,A1 .Location in patent: Paragraph 00471

6
[ 1050501-88-6 ]
[ 1266114-83-3 ]

Reference： [1]Patent: WO2012/80450,2012,A1
[2]Patent: WO2013/186335,2013,A1
[3]Patent: WO2013/186333,2013,A1
[4]Patent: WO2014/60411,2014,A1
[5]Patent: US2015/111868,2015,A1

7
[ 1050501-88-6 ]
[ 1383252-82-1 ]

Reference： [1]Patent: WO2012/80450,2012,A1
[2]Patent: WO2014/60411,2014,A1

8
[ 1050501-88-6 ]
[ 1383252-83-2 ]

Reference： [1]Patent: WO2012/80450,2012,A1
[2]Patent: WO2014/60411,2014,A1

9
[ 1050501-88-6 ]
[ 1199556-78-9 ]
C₂₀H₂₁ClN₂O₄ [ No CAS ]