[ CAS No. 507462-51-3 ] {[proInfo.proName]}

Name: 507462-51-3|5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-amine|97%
Brand: Ambeed
SKU: A173155
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Quality Control of [ 507462-51-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 507462-51-3 ]

Product Details of [ 507462-51-3 ]

CAS No. :	507462-51-3	MDL No. :	MFCD17012797
Formula :	C₇H₆BrN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JMCVFWQJWKRMHW-UHFFFAOYSA-N
M.W :	212.05	Pubchem ID :	66521758
Synonyms :

Calculated chemistry of [ 507462-51-3 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	48.2
TPSA :	54.7 Å²

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) :	-6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.27
Log Po/w (XLOGP3) :	1.32
Log Po/w (WLOGP) :	1.92
Log Po/w (MLOGP) :	1.13
Log Po/w (SILICOS-IT) :	1.99
Consensus Log Po/w :	1.53

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.59
Solubility :	0.543 mg/ml ; 0.00256 mol/l
Class :	Soluble
Log S (Ali) :	-2.07
Solubility :	1.81 mg/ml ; 0.00852 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.41
Solubility :	0.0823 mg/ml ; 0.000388 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.75

Safety of [ 507462-51-3 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340	UN#:
Hazard Statements:	H302	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 507462-51-3 ]

* 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 [ 507462-51-3 ]

[ 507462-51-3 ] Synthesis Path-Downstream 1~56

1
[ 401647-24-3 ]
[ 507462-51-3 ]
[ 1449318-35-7 ]

Yield	Reaction Conditions	Operation in experiment
31%	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 4h;	1.3 Step 3: Preparation of Title compound: 1 -Benzyl-1 H-pyrazole-4-carboxylic acid (5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-amide 5-Bromo-1 H-pyrrolo[2,3-b]pyridin-3-ylamine (60mg, 0.28mmol), 1 -benzyl-1 H- pyrazole-4-carboxylic acid (62mg, 0.31 mmol) and triethylamine (57mg, 80uL, 0.56mmol) were stirred in dimethyl formamide (1 ml_). 0-(7-azabenzotriazol-1-yl)- Ν,Ν,Ν',Ν'-tetramethyluroniumhexafluorophosphate (HATU) (106mg, 0.28mmol) was added and the reaction was stirred at room temperature for 4 hours. The reaction mixture was partitioned between EtOAc and saturated sodium hydrogen sulphate solution and the organics separated and washed with saturated aqueous sodium chloride (x4), dried (MgS04) and solvent removed in vacuo to afford a brown solid. The residue was purified by flash chromatography on Si02 eluting first with 50% E tO Ac/DC M and then 5% MeOH/DCM. The fractions containing pure product were combined and concentrated in vacuo to afford the title compound as a tan solid, 35mg, 31 %. LC/MS: RT = 2.22 Min (270nm), m/z = 396 [M+H], 394 [M-H]. Total run time 3.75 min (short pos/neg), HP1 100. 1H NMR (d6 DMSO): 55.41 (s, 2H), 7.28-7.41 (m, 5H), 7.84 (d, 1 H), 8.08 (s, 1 H), 8.28 (d, 1 H), 8.45 (s, 1 H), 8.48 (d, 1 H), 9.88 (s, 1 H), 11.69 (br s, 1 H)
31%	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 4h;	1.3 Step 3: Preparation of Title compound: 1-Benzyl-1H-pyrazole-4-carboxylic acid (5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-amide 5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-ylamine (60 mg, 0.28 mmol), 1-benzyl-1H-pyrazole-4-carboxylic acid (62 mg, 0.31 mmol) and triethylamine (57 mg, 80 uL, 0.56 mmol) were stirred in dimethyl formamide (1 mL). O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluroniumhexafluorophosphate (HATU) (106 mg, 0.28 mmol) was added and the reaction was stirred at room temperature for 4 hours. The reaction mixture was partitioned between EtOAc and saturated sodium hydrogen sulphate solution and the organics separated and washed with saturated aqueous sodium chloride (*4), dried (MgSO4) and solvent removed in vacuo to afford a brown solid. The residue was purified by flash chromatography on SiO2 eluting first with 50% EtOAc/DCM and then 5% MeOH/DCM. The fractions containing pure product were combined and concentrated in vacuo to afford the title compound as a tan solid, 35 mg, 31%. LC/MS: RT=2.22 Min (270 nm), m/z=396 [M+H], 394 [M-H]. Total run time 3.75 min (short pos/neg), HP1100. 1H NMR (d6 DMSO): δ5.41 (s, 2H), 7.28-7.41 (m, 5H), 7.84 (d, 1H), 8.08 (s, 1H), 8.28 (d, 1H), 8.45 (s, 1H), 8.48 (d, 1H), 9.88 (s, 1H), 11.69 (br s, 1H)

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1 Location in patent: Page/Page column 23; 24
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1 Location in patent: Paragraph 0099; 0103; 0104; 0105

2
[ 507462-51-3 ]
[ 1449320-92-6 ]
[ 1449320-90-4 ]

Yield	Reaction Conditions	Operation in experiment
22.3%	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 72h;	70.5 Step 5: Preparation of title compound: 1 -(1 H-pyrrol-2-ylmethyl)-1 H-pyrazole-4- carboxylic acid (5-bromo-1 H-pyrrolo[2,3-b]pyridin-3-yl)-amide 5-Bromo-1 H-pyrrolo[2,3-b]pyridin-3-ylamine (101.8mg, 0.48mmol) and potassium 1 -(1 H-pyrrol-2-ylmethyl)-1 H-pyrazole-4-carboxylate (61.2mg, 0.179mmol) were stirred in DMF (4ml_) and triethylamine (97mg, 0.13ml, 0.96mmol) was added followed by HATU (183mg, 0.48mmol) . The reaction mixture was left to stir at RT for 72 hours and diluted with EtOAc. The organics were separated and the aqueous extracted with a further portion of EtOAc. The combined extracts were washed with saturated aqueous sodium chloride (x3), dried (MgSO4) and concentrated in vacuo. The crude material was purified automated flash chromatography eluting with DCM to 20% MeOH / DCM (gradient). Fractions containing product were combined and concentrated in vacuo and the residue was further purified by preparative HPLC at pH9 to afford the title compound as a white solid, 15.4mg, 22.3%. LC/MS: RT = 1.09 Min (254nm), m/z = 386.0 [M+H]. Total run time 1.9 min (super short pos),HP1200. 1H NMR (d6 DMSO): 55.28 (s, 2H), 6.00 (m, 1H), 6.13 (s, 1H), 6.75 (m, 1H), 7.83 (d, 1H), 8.04 (s, 1H), 8.23 (s, 1H), 8.27 (d, 1H), 8.47 (d, 1H), 9.88 (s, 1H), 11.03 (s, 1H), 11.69 (s, 1H)
22.3%	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 72h;	70.5 Step 5: Preparation of title compound: 1-(1H-pyrrol-2-ylmethyl)-1H-pyrazole-4-carboxylic acid (5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-amide 5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-ylamine (101.8 mg, 0.48 mmol) and potassium 1-(1H-pyrrol-2-ylmethyl)-1H-pyrazole-4-carboxylate (61.2 mg, 0.179 mmol) were stirred in DMF (4 mL) and triethylamine (97 mg, 0.13 ml, 0.96 mmol) was added followed by HATU (183 mg, 0.48 mmol). The reaction mixture was left to stir at RT for 72 hours and diluted with EtOAc. The organics were separated and the aqueous extracted with a further portion of EtOAc. The combined extracts were washed with saturated aqueous sodium chloride (*3), dried (MgSO4) and concentrated in vacuo. The crude material was purified automated flash chromatography eluting with DCM to 20% MeOH/DCM (gradient). Fractions containing product were combined and concentrated in vacuo and the residue was further purified by preparative HPLC at pH9 to afford the title compound as a white solid, 15.4 mg, 22.3%. LC/MS: RT=1.09 Min (254 nm), m/z=386.0 [M+H]. Total run time 1.9 min (super short pos), HP1200. 1H NMR (d6 DMSO): δ 5.28 (s, 2H), 6.00 (m, 1H), 6.13 (s, 1H), 6.75 (m, 1H), 7.83 (d, 1H), 8.04 (s, 1H), 8.23 (s, 1H), 8.27 (d, 1H), 8.47 (d, 1H), 9.88 (s, 1H), 11.03 (s, 1H), 11.69 (s, 1H)

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1 Location in patent: Page/Page column 107; 108
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1 Location in patent: Paragraph 0460; 0461; 0462

3
[ 183208-35-7 ]
[ 507462-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: nitric acid / 0.5 h / 0 °C 2: acetic acid; tin(II) chloride dihdyrate; hydrogenchloride / 2 h / 85 °C
	Multi-step reaction with 2 steps 1: nitric acid / water / 0.5 h / 0 °C 2: acetic acid; tin(II) chloride dihdyrate / 2 h / 85 °C
	Multi-step reaction with 2 steps 1: nitric acid / 5 h / 70 °C 2: hydrogenchloride; tin(II) chloride dihdyrate / water / 2 h / 0 - 20 °C

	Multi-step reaction with 2 steps 1: potassium nitrate; sulfuric acid / 0.25 h / -5 - 0 °C 2: zinc; ammonium chloride / ethanol / 4 h / 65 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: sulfuric acid; potassium nitrate / 0.25 h / -5 - 0 °C 2: zinc; ammonium chloride / ethanol / 4 h / 65 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1
[3]Current Patent Assignee: HEPAREGENIX GMBH - WO2018/134254, 2018, A1
[4]Current Patent Assignee: CHENGDU ACHI BIOPHARMACEUTICAL TECH; CHENGDU TIANTAISHAN PHARMACEUTICAL; SHANGHAI PUYUAN MEDICAL TECH CENTER - CN109942574, 2019, A
[5]Current Patent Assignee: SICHUAN GUOKANG PHARMACEUTICAL - CN110105356, 2019, A

4
[ 507462-26-2 ]
[ 507462-51-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With ammonium chloride; zinc; In ethanol; at 65℃; for 4.0h;Inert atmosphere;	Compound 2 (6.0 g, 0.025 mol), zinc powder (8.3 g, 0.127 mol), ammonium chloride (16 g, 0.302 mol), and anhydrous ethanol 250 ml were added to a 500 ml reaction flask.Protected with nitrogen, heated to 65 C, and stirred for 4 hours. Cool to room temperature, filter,The solvent was concentrated under reduced pressure to give 3-amino-5-bromo-7-azaindole (Compound 3).It weighed 5.0 g and the yield was 94%.
94%	With ammonium chloride; zinc; In ethanol; at 65℃; for 4.0h;Inert atmosphere;	Compound 2 (6.0 g, 0.025 mol) was added to a 500 ml reaction flask.Zinc powder (8.3 g, 0.127 mol),Ammonium chloride (16 g, 0.302 mol),250 ml of absolute ethanol, protected with nitrogen, heated to 65 C, and stirred for 4 hours.Cool to room temperature, filter, and concentrate under reduced pressure to remove solvent.Obtaining 3-amino-5-bromo-7-azaindole (compound 3),Weighing 5.0 grams, the yield was 94%.
66%	With hydrogenchloride; tin(II) chloride dihdyrate; acetic acid; at 85℃; for 2.0h;	5-Bromo-3-nitro-1H-pyrrolo[2,3-b]pyridine was stirred in glacial acetic acid (6mL)at 85C and to this, was added a solution of tin(ll)chloride dihydrate (936mg,4.1 5mmol) in conc. HCl (1 mL), drop wise. After addition the reaction was heated at 85C for a further 2 hours and then allowed to cool to room temperature. The reaction mixture was poured onto a mixture of rapidly stirring ice/H2O (30mL) and the pH was adjusted to 9 by the careful addition of a 50% aqueous solutionof sodium hydroxide. This aqueous mixture was extracted with DCM (3x25mL) and the combined extracts were washed with H2O, saturated aqueous sodium chloride, dried (MgSO4) and concentrated in vacuo to yield the desired compound, 115mg, 66%.

66%

With tin(II) chloride dihdyrate; acetic acid; at 85℃; for 2.0h;

5-Bromo-3-nitro-1H-pyrrolo[2,3-b]pyridine was stirred in glacial acetic acid (6 mL) at 85 C. and to this, was added a solution of tin(II)chloride dihydrate (936 mg, 4.15 mmol) in conc. HCl (1 mL), drop wise. After addition the reaction was heated at 85 C. for a further 2 hours and then allowed to cool to room temperature. The reaction mixture was poured onto a mixture of rapidly stirring ice/H2O (30 mL) and the pH was adjusted to 9 by the careful addition of a 50% aqueous solution of sodium hydroxide. This aqueous mixture was extracted with DCM (3*25 mL) and the combined extracts were washed with H2O, saturated aqueous sodium chloride, dried (MgSO4) and concentrated in vacuo to yield the desired compound, 115 mg, 66%.

Reference： [1]Patent: CN109942574,2019,A .Location in patent: Paragraph 0044; 0048-0050
[2]Patent: CN110105356,2019,A .Location in patent: Paragraph 0070-0071; 0076-0077
[3]Patent: WO2013/114113,2013,A1 .Location in patent: Page/Page column 23; 24
[4]Patent: US2015/11533,2015,A1 .Location in patent: Paragraph 0102
[5]Patent: WO2018/134254,2018,A1 .Location in patent: Page/Page column 78; 79

5
[ 507462-51-3 ]
[ 1449319-61-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation
	Multi-step reaction with 2 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

6
[ 507462-51-3 ]
[ 1449319-59-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 3.1: tetrahydrofuran / 0.17 h / 20 °C 3.2: 18 h / 20 °C
	Multi-step reaction with 3 steps 1.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 3.1: tetrahydrofuran / 0.17 h / 20 °C 3.2: 18 h / 20 °C

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

7
[ 507462-51-3 ]
[ 1449319-63-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 3: hydrogen; palladium 10% on activated carbon; acetic acid / N,N-dimethyl-formamide / 40 h / 45 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 3: acetic acid; palladium 10% on activated carbon; hydrogen / N,N-dimethyl-formamide / 40 h / 45 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

8
[ 507462-51-3 ]
[ 1449319-69-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 3.1: tetrahydrofuran / 0.17 h / 20 °C 3.2: 18 h / 20 °C
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 3: tetrahydrofuran / 0.17 h / 20 °C

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

9
[ 507462-51-3 ]
[ 1449319-84-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C
	Multi-step reaction with 2 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

10
[ 507462-51-3 ]
[ 1449319-87-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

11
[ 507462-51-3 ]
[ 1449319-89-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 4.1: tetrahydrofuran / 3 h / 20 °C / Molecular sieve 4.2: 18 h / 20 °C
	Multi-step reaction with 4 steps 1.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 4.1: tetrahydrofuran; methanol / 3 h / 20 °C / Molecular sieve 4.2: 18 h / 20 °C / Molecular sieve

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

12
[ 507462-51-3 ]
[ 1449319-82-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 4.1: tetrahydrofuran / 3 h / 20 °C / Molecular sieve 4.2: 18 h / 20 °C 5.1: potassium hydroxide; water / tetrahydrofuran; methanol / 18 h / 20 °C
	Multi-step reaction with 5 steps 1.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 4.1: tetrahydrofuran; methanol / 3 h / 20 °C / Molecular sieve 4.2: 18 h / 20 °C / Molecular sieve 5.1: potassium hydroxide; water / tetrahydrofuran; methanol / 18 h / 20 °C

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

13
[ 507462-51-3 ]
[ 1449319-96-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 4.1: tetrahydrofuran / 3 h / 20 °C / Molecular sieve 4.2: 18 h / 20 °C 5.1: potassium carbonate / methanol / 0.5 h / 100 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

14
[ 507462-51-3 ]
[ 1449319-98-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 4.1: tetrahydrofuran / 3 h / 20 °C / Molecular sieve 4.2: 18 h / 20 °C

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

15
[ 507462-51-3 ]
1-benzyl-1H-pyrazol-4-carboxylic acid [5-(5-formylthiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran; 1,4-dioxane / 2 h / 150 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

16
[ 507462-51-3 ]
[ 1449320-04-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran; 1,4-dioxane / 2 h / 150 °C / Microwave irradiation 4.1: tetrahydrofuran / 3 h / 20 °C / Molecular sieve 4.2: 18 h / 20 °C

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

17
[ 507462-51-3 ]
C₃₀H₂₃N₅O₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 0.33 h / 150 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

18
[ 507462-51-3 ]
C₃₄H₃₂N₆O₃S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 0.33 h / 150 °C / Microwave irradiation 4.1: tetrahydrofuran / 3 h / 20 °C / Molecular sieve 4.2: 18 h / 20 °C

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

19
[ 507462-51-3 ]
[ 1449320-08-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 0.33 h / 150 °C / Microwave irradiation 4.1: tetrahydrofuran / 3 h / 20 °C / Molecular sieve 4.2: 18 h / 20 °C 5.1: methanol; potassium carbonate / 0.5 h / 100 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

20
[ 507462-51-3 ]
[ 1449320-11-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 0.33 h / 150 °C / Microwave irradiation 4.1: tetrahydrofuran / 3 h / 20 °C / Molecular sieve 4.2: 18 h / 20 °C 5.1: methanol; potassium carbonate / 0.5 h / 100 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

21
[ 507462-51-3 ]
[ 1449320-32-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

22
[ 507462-51-3 ]
[ 1449320-30-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 4: caesium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

23
[ 507462-51-3 ]
[ 1449320-25-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 4: caesium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C 5: potassium carbonate / methanol / 0.5 h / 100 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

24
[ 507462-51-3 ]
C₃₈H₄₀N₆O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 4: caesium carbonate / N,N-dimethyl-formamide / 18 h / 60 °C

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

25
[ 507462-51-3 ]
[ 1449320-34-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 4: caesium carbonate / N,N-dimethyl-formamide / 18 h / 60 °C 5: potassium carbonate / methanol / 0.5 h / 100 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

26
[ 507462-51-3 ]
C₃₈H₃₈N₆O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 4: caesium carbonate / N,N-dimethyl-formamide / 18 h / 70 °C

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

27
[ 507462-51-3 ]
[ 1449320-39-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 4: caesium carbonate / N,N-dimethyl-formamide / 18 h / 70 °C 5: potassium carbonate / methanol / 0.5 h / 100 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

28
[ 507462-51-3 ]
[ 1449320-27-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: sodium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 1.5 h / 140 °C / Microwave irradiation; Inert atmosphere
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: sodium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 1.5 h / 140 °C / Inert atmosphere; Microwave irradiation

29
[ 507462-51-3 ]
[ 1449320-47-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: butan-1-ol / 60 h / 160 °C / Sealed tube

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

30
[ 507462-51-3 ]
C₃₂H₂₄FN₅O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate / water; acetonitrile / 2 h / 130 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

31
[ 507462-51-3 ]
[ 1449320-71-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate / water; acetonitrile / 2 h / 130 °C / Microwave irradiation 4.1: tetrahydrofuran / 3 h / 20 °C / Molecular sieve 4.2: 18 h / 20 °C

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

32
[ 507462-51-3 ]
[ 1449318-43-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation
	Multi-step reaction with 2 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

33
[ 507462-51-3 ]
C₃₅H₃₂N₆O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

34
[ 507462-51-3 ]
[ 1449320-73-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 4: potassium hydroxide; water / tetrahydrofuran; methanol / 18 h / 20 °C

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

35
[ 507462-51-3 ]
C₂₉H₂₅N₇O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 0.33 h / 150 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

36
[ 507462-51-3 ]
[ 1449320-76-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 0.33 h / 150 °C / Microwave irradiation 4: potassium hydroxide; water / tetrahydrofuran; methanol / 18 h / 20 °C

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

37
[ 507462-51-3 ]
[ 1449320-78-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; 1,4-dioxane / 1 h / 120 °C / Microwave irradiation
	Multi-step reaction with 2 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; 1,4-dioxane / 1 h / 120 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

38
[ 507462-51-3 ]
[ 1449321-20-3 ]
[ 1449321-22-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water / tetrahydrofuran / 1 h / 130 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

39
[ 507462-51-3 ]
[ 1449321-15-6 ]
[ 1449321-24-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water / tetrahydrofuran / 1 h / 130 °C / Microwave irradiation 3.2: 0.5 h / 80 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

40
[ 507462-51-3 ]
[ 1449321-28-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 4 h / 120 - 140 °C / Microwave irradiation
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 4 h / 120 - 140 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

41
[ 507462-51-3 ]
[ 1449321-30-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 4 h / 120 - 140 °C / Microwave irradiation 4: potassium carbonate / N,N-dimethyl-formamide / 16 h / 50 °C
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 16 h / 50 °C

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

42
[ 507462-51-3 ]
[ 1449321-26-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 4 h / 120 - 140 °C / Microwave irradiation 4: potassium carbonate / N,N-dimethyl-formamide / 16 h / 50 °C 5: methanol; potassium carbonate / 0.5 h / 100 °C / Microwave irradiation
	Multi-step reaction with 4 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 16 h / 50 °C 4: potassium carbonate; methanol / 0.5 h / 100 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

43
[ 507462-51-3 ]
[ 1449321-32-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: sodium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 1.5 h / 140 °C / Microwave irradiation; Inert atmosphere 4: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1.5 h / 130 °C / Microwave irradiation
	Multi-step reaction with 4 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 4: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1.5 h / 130 °C / Microwave irradiation
	Multi-step reaction with 4 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: sodium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 1.5 h / 140 °C / Inert atmosphere; Microwave irradiation 4: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1.5 h / 130 °C / Microwave irradiation

44
[ 507462-51-3 ]
[ 1449318-45-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: 2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl; chloro-(2-dicyclohexylphosphino-2′,6′-diiso-propoxy-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl-tert-butyl ether adduct; lithium hexamethyldisilazane / tetrahydrofuran / 18 h / 65 °C / Sealed tube; Inert atmosphere
	Multi-step reaction with 2 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: ruphos; lithium hexamethyldisilazane; chloro-(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-tert-butyl ether adduct / tetrahydrofuran / 18 h / 65 °C / Inert atmosphere; Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

45
[ 507462-51-3 ]
[ 1449321-31-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: sodium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 1.5 h / 140 °C / Microwave irradiation; Inert atmosphere 4: potassium carbonate / methanol / 0.5 h / 80 °C / Microwave irradiation
	Multi-step reaction with 5 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: sodium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 1.5 h / 140 °C / Inert atmosphere; Microwave irradiation 4: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1.5 h / 130 °C / Microwave irradiation 5: potassium carbonate; methanol / 0.5 h / 80 °C / Microwave irradiation
	Multi-step reaction with 5 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 4: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1.5 h / 130 °C / Microwave irradiation 5: potassium carbonate; methanol / 0.5 h / 80 °C / Microwave irradiation

46
[ 507462-51-3 ]
C₃₃H₂₈F₂N₆O₃S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 0.33 h / 150 °C / Microwave irradiation 4.1: tetrahydrofuran / 3 h / 20 °C / Molecular sieve 4.2: 18 h / 20 °C

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2013/114113, 2013, A1

47
[ 507462-51-3 ]
1-benzyl-1H-pyrazol-4-carboxylic acid [5-(4-pyrrolidin-1-ylmethylphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]amide formate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 3: tetrahydrofuran / 0.17 h / 20 °C

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

48
[ 507462-51-3 ]
1-benzyl-1H-pyrazol-4-carboxylic acid [5-(4-dimethylaminomethylphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]amide formate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 120 °C / Microwave irradiation 3: acetic acid; palladium 10% on activated carbon; hydrogen / N,N-dimethyl-formamide / 40 h / 45 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

49
[ 507462-51-3 ]
[ 1449321-15-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 130 °C / Microwave irradiation 4: potassium carbonate; methanol / 0.5 h / 80 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

50
[ 507462-51-3 ]
[ 1449321-20-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 4 h / 20 °C 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 1 h / 130 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2015/11533, 2015, A1

51
[ 1103234-56-5 ]
[ 507462-51-3 ]
N-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide [ No CAS ]

Reference： [1]Patent: WO2018/134254,2018,A1

52
[ 1103234-56-5 ]
[ 507462-51-3 ]
C₁₇H₁₅BrF₂N₄O₃S [ No CAS ]

Reference： [1]Patent: WO2018/134254,2018,A1 .Location in patent: Page/Page column 78; 79

53
[ 507462-51-3 ]
C₁₉H₂₃ClF₃N₃O₃*H⁽¹⁺⁾ [ No CAS ]
C₂₆H₂₈BrF₃N₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.6 g	With triethylamine In tetrahydrofuran at 20℃;	1.3 Step 3: Synthesis of Compound 5 Compound 4 (10 g, 0.024 mol), 300 ml of dichloromethane, and 4 ml of DMF were added to a 500 ml reaction flask, and 4 ml of oxalyl chloride was slowly added dropwise, and the mixture was stirred at room temperature for 2 hours, and concentrated under reduced pressure to give an acid chloride. Another 500 ml reaction flask was taken and compound 3 (5 g, 0.024 mol) was added.5 ml of triethylamine, 150 ml of tetrahydrofuran, and a solution of a spare acid chloride in 150 ml of tetrahydrofuran were added dropwise with stirring. Stir at room temperature overnight.Concentrated the next morning and the residue was purified by column chromatography (dichloromethane:methanol = 20:1).The product was obtained as a white solid (yield 3.6 g, yield: 25%).

Reference： [1]Current Patent Assignee: CHENGDU ACHI BIOPHARMACEUTICAL TECH; CHENGDU TIANTAISHAN PHARMACEUTICAL; SHANGHAI PUYUAN MEDICAL TECH CENTER - CN109942574, 2019, A Location in patent: Paragraph 0044; 0051-0054

54
[ 507462-51-3 ]
C₃₂H₃₂F₅N₇O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 20 °C 2: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate; palladium diacetate / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: CHENGDU ACHI BIOPHARMACEUTICAL TECH; CHENGDU TIANTAISHAN PHARMACEUTICAL; SHANGHAI PUYUAN MEDICAL TECH CENTER - CN109942574, 2019, A

55
[ 507462-51-3 ]
C₃₀H₃₃F₂N₇O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 20 °C 2: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate; palladium diacetate / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere 3: triethylamine / methanol / 65 °C

Reference： [1]Current Patent Assignee: CHENGDU ACHI BIOPHARMACEUTICAL TECH; CHENGDU TIANTAISHAN PHARMACEUTICAL; SHANGHAI PUYUAN MEDICAL TECH CENTER - CN109942574, 2019, A

56
[ 507462-51-3 ]
C₂₀H₂₆ClF₃N₃O₃⁽¹⁺⁾ [ No CAS ]
C₂₆H₂₈BrF₃N₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With triethylamine In tetrahydrofuran at 20℃;	1.3 Step 3: Synthesis of N-(5-bromo-1H-pyrazolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)-2-(2,2,2-tri Fluorine-N-(tetrahydro-2H-pyran-4-yl)acetamido)benzamide (Compound 5) Compound 4 (10 g, 0.024 mol) was added to a 500 ml reaction flask.300 ml of dichloromethane, 4 drops of DMF, 4 ml of oxalyl chloride was slowly added dropwise, and the mixture was stirred at room temperature for 2 hours, and concentrated under reduced pressure to give an acid chloride.Another 500 ml reaction flask was taken, and compound 3 (5 g, 0.024 mol), 5 ml of triethylamine, 150 ml of tetrahydrofuran were added, and a solution of the acid chloride in 150 ml of tetrahydrofuran was added dropwise with stirring.Stir at room temperature overnight.Concentrated the next morning and the residue was chromatographed (dichloromethane:methanol = 20:1).Obtaining a white solid product compound 5,Weighing 3.6 grams, the yield is 25%.

Reference： [1]Current Patent Assignee: SICHUAN GUOKANG PHARMACEUTICAL - CN110105356, 2019, A Location in patent: Paragraph 0070-0071; 0078-0081

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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 507462-51-3 ] {[proInfo.proName]}

Quality Control of [ 507462-51-3 ]

Related Doc. of [ 507462-51-3 ]

Product Details of [ 507462-51-3 ]

Calculated chemistry of [ 507462-51-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 507462-51-3 ]

Application In Synthesis of [ 507462-51-3 ]

[ 507462-51-3 ] Synthesis Path-Downstream 1~56

Related Functional Groups of [ 507462-51-3 ]

Bromides

Amines

Related Parent Nucleus of [ 507462-51-3 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 507462-51-3 ]

Related Parent Nucleus of
[ 507462-51-3 ]