916325-85-4|5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid| Ambeed

Structure of 916325-85-4

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Quality Control of [ 916325-85-4 ] Purity: 98% SDS Specification

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Product Details of [ 916325-85-4 ]

CAS No. :	916325-85-4
Formula :	C₇H₄BrN₃O₂
M.W :	242.03
SMILES Code :	OC(=O)C1=NNC2=C1C=C(Br)C=N2
MDL No. :	MFCD11040726
InChI Key :	JSXAWNXOASHZLY-UHFFFAOYSA-N
Pubchem ID :	45480265

Safety of [ 916325-85-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 916325-85-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	4.0
Num. H-bond donors	2.0
Molar Refractivity	48.55
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	78.87 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.67
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.37
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.42
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.99
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.57
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.2

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.65
Solubility	0.542 mg/ml ; 0.00224 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.63
Solubility	0.569 mg/ml ; 0.00235 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.77
Solubility	0.41 mg/ml ; 0.00169 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.8 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.85

Application In Synthesis of [ 916325-85-4 ]

* 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 [ 916325-85-4 ]

[ 916325-85-4 ] Synthesis Path-Downstream 1~41

1
[ 916325-85-4 ]
[ 916325-86-5 ]
[ 948834-63-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.

2
[ 916325-85-4 ]
[ 54998-08-2 ]
[ 948834-64-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.

3
[ 916325-85-4 ]
[ 119421-28-2 ]
[ 948834-65-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.

4
[ 916325-85-4 ]
[ 916326-41-5 ]
[ 948834-70-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.

5
[ 916325-85-4 ]
[ 107582-20-7 ]
C₁₅H₁₂N₅O₃Br [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.

6
[ 916325-84-3 ]
[ 916325-85-4 ]

Yield	Reaction Conditions	Operation in experiment
100%		Compound Ib (3.4 g, 13.2 mmol) in MeOH (50 mL) was refluxed with 2MNaOH (10 mL) for 4 hrs. The mixture was cooled to room temperature and acidified with hydrochloric acid to give Compound Ic (3.22 g, 100%). 1H NMR (300 MHz,CD3OD) delta 8.62 (s, IH), 8.58 (s, IH);' MS (ESI) m/z: 359 (M+H+).
92%		Step 7[00181] A suspension of methyl 5-bromo-lH-pyrazolo[3,4-£]pyridine-3- carboxylate (VII) (70 mg, 0.27 mmol) in aqueous IN NaOH solution (20 mL) was heated at 90C for 3 h until the solution became clear. The solution was then cooled to 0C and acidified with a 10%> HC1 solution. The solids formed were filtered, washed with cold water and dried at room temperature under vacuum to give 5-bromo-lH-pyrazolo[3,4- £]pyridine-3-carboxylic acid (VIII) as a white solid (60 mg, 0.25 mmol, 92% yield). 1H NMR (CDCls) delta ppm 8.58 (d, J=3.01 Hz, 1 H), 8.66 (d, J=3.01 Hz, 1 H); ESIMS found for C7H4BrN302 mlz 242.1 (M+H).
92%		spension of methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (XVII) (70 mg, 0.27 mmol) in aqueous 1N NaOH solution (20 mL) was heated at 90 C. for 3 h until the solution became clear. The solution was then cooled to 0 C. and acidified with a 10% HCl solution. The solids formed were filtered, washed with cold water and dried at room temperature under vacuum to give 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XVIII) as a white solid (60 mg, 0.25 mmol, 92% yield). 1H NMR (CDCl3) delta ppm 8.58 (d, J=3.01 Hz, 1H), 8.66 (d, J=3.01 Hz, 1H); ESIMS found for C7H4BrN3O2 m/z 242.1 (M+H).

92%	With water; sodium hydroxide; at 90℃; for 3h;	Step 7 A suspension of methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (XV) (70 mg, 0.27 mmol) in aqueous 1N NaOH solution (20 mL) was heated at 90 C. for 3 h until the solution became clear. The solution was then cooled to 0 C. and acidified with a 10% HCl solution. The solids formed were filtered, washed with cold water and dried at room temperature under vacuum to give 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XVI) as a white solid (60 mg, 0.25 mmol, 92% yield). 1H NMR (CDCl3) delta ppm 8.58 (d, J=3.01 Hz, 1H), 8.66 (d, J=3.01 Hz, 1H); ESIMS found for C7H4BrN3O2 m/z 242.1 (M+H).
92%	With water; sodium hydroxide; at 0 - 90℃; for 3h;	A suspension of methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (XV) (70 mg, 0.27 mmol) in aqueous IN NaOH solution (20 mL) was heated at 90C for 3 h until the solution became clear. The solution was then cooled to 0C and acidified with a 10% HC1 solution. The solids formed were filtered, washed with cold water and dried at room temperature under vacuum to give 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XVI) as a white solid (60 mg, 0.25 mmol, 92% yield). 1H NMR (CDCl3) delta ppm 8.58 (d, J=3.01Hz, 1H), 8.66 (d, J=3.01Hz, 1H); ESIMS found for C7H4BrN3O2 m/z 242.1 (M+H).

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.
[2]Patent: WO2006/130673,2006,A1 .Location in patent: Page/Page column 74.
[3]Patent: WO2011/84486,2011,A1 .Location in patent: Page/Page column 106; 112-113.
[4]Patent: US2013/296302,2013,A1 .Location in patent: Paragraph 0499.
[5]Patent: US2016/68550,2016,A1 .Location in patent: Paragraph 1061.
[6]Patent: WO2016/40193,2016,A1 .Location in patent: Paragraph 0708.

7
[ 916325-85-4 ]
[ 916325-81-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.

8
[ 916325-85-4 ]
[ 916326-95-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.
[2]Patent: WO2006/130673,2006,A1 .

9
[ 916325-85-4 ]
C₁₇H₁₅N₆OBr [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.

10
[ 916325-85-4 ]
[ 916326-43-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.
[2]Patent: WO2006/130673,2006,A1 .

11
[ 916325-85-4 ]
[ 916326-44-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.
[2]Patent: WO2006/130673,2006,A1 .

12
[ 916325-85-4 ]
[ 916326-45-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.
[2]Patent: WO2006/130673,2006,A1 .

13
[ 916325-85-4 ]
[ 916326-40-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.
[2]Patent: WO2006/130673,2006,A1 .

14
[ 916325-85-4 ]
C₂₄H₁₈N₆O₃S [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.
[2]Patent: WO2006/130673,2006,A1 .

15
[ 916325-85-4 ]
4-[3-(4-isopropoxymethyl-1H-benzoimidazol-2-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-isoquinoline [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.

16
[ 916325-85-4 ]
isopropyl-[2-(5-isoquinolin-4-yl-1H-pyrazolo[3,4-b]pyridin-3-yl)-1H-benzoimidazol-4-ylmethyl]-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.

17
[ 916325-85-4 ]
diethyl-[2-(5-isoquinolin-4-yl-1H-pyrazolo[3,4-b]pyridin-3-yl)-1H-benzoimidazol-4-ylmethyl]-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.

18
[ 916325-85-4 ]
[ 916326-58-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.
[2]Patent: WO2006/130673,2006,A1 .

19
[ 916325-85-4 ]
[ 916326-59-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.
[2]Patent: WO2006/130673,2006,A1 .

20
[ 916325-85-4 ]
[ 916326-56-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.
[2]Patent: WO2006/130673,2006,A1 .

21
[ 916325-85-4 ]
[ 916326-60-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.
[2]Patent: WO2006/130673,2006,A1 .

22
[ 916325-85-4 ]
2-(5-isoquinolin-4-yl-1H-pyrazolo[3,4-b]pyridin-3-yl)-1H-benzoimidazole-4-carboxylic acid isopropylamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.
[2]Patent: WO2006/130673,2006,A1 .

23
[ 916325-85-4 ]
2-(5-isoquinolin-4-yl-1H-pyrazolo[3,4-b]pyridin-3-yl)-1H-benzoimidazole-4-carboxylic acid diethylamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.

24
[ 916325-83-2 ]
[ 916325-85-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4297 - 4302.
[2]Patent: WO2011/84486,2011,A1 .
[3]Patent: US2013/296302,2013,A1 .
[4]Patent: US2016/68550,2016,A1 .
[5]Patent: WO2016/40193,2016,A1 .
[6]Patent: WO2006/130673,2006,A1 .

25
[ 916325-85-4 ]
[ 107582-20-7 ]
2-amino-3-[(5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carbonyl)-amino]-benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃;	A mixture of 5-bromo-lEta-pyrazolo[3,4-b]pyridine-3-carboxylic acid Compound Ic (0.3 g, 1.17 mmol), 2,3-diamino-benzoic acid methyl ester Compound 8a (3.43 g, 20.64 mmol), HATU (7.85 g, 20.66 mmol), DIPEA (8.64 mL, 62 mmol) in DMF (250 mL) was stirred at room temperature overnight. The solvent was removed and the residue was purified by silica gel chromatography (10% to 90% of ethyl acetate in hexanes) to yield 2-amino-3-[(5-bromo-lH-pyrazolo[3,4-b]pyridine-3-carbonyl)- amino] -benzoic acid methyl ester Compound 8b (5.1 g, 63% yield) as a colorless gel. 1H NMR (300 MHz, CD3OD) delta 9.03 (d, IH, J = 2.1 Hz), 8.78 (d, IH, J = 2.1 Hz), 7.58 (d, IH, 7= 7.8 Hz), 7.26 (d, IH, 7= 7.8 Hz), 7.15 (t, IH, 7 = 7.8 Hz), 3.49 (s, 3H); MS (ESI) m/z: 391 (M+H+).

References: [1]Patent: WO2006/130673,2006,A1 .Location in patent: Page/Page column 95.

26
[ 916325-85-4 ]
[ 658-89-9 ]
5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (2-amino-4-trifluoromethoxy-phenyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃;	A mixture of S-bromo-lH-pyrazoloP^-bjpyridine-S-carboxyric acid Compound Ic (0.68 g, 1.93 mmol), Compound 16b (0.373 g, 1.93 mmol), HATU (0.73 g, 1.9 mmol) and DIPEA (1 mL, 5.8 mmol) in DMF (30 mL) was stirred at room temperature overnight. The solvent was removed under vacuum and the resulting yellow residue was mixed with AcOEt, sequentially washed with saturated aqueous NH4Cl, IM HCl, water and saturated aqueous NaHCO3, then dried over Na2SO4. The solvent was evaporated to dryness to provide 5-bromo-lH-pyrazolo[3,4-b]pyridine-3- carboxylic acid (2-amino-4-trifluoromethoxy-phenyl)-amide Compound 16c (0.67 g, 83% yield) as a yellow solid. LC-MS major peak 3.03 min, MS (ESI) m/z 416.0 (M+)/417.0 (M+H+).

References: [1]Patent: WO2006/130673,2006,A1 .Location in patent: Page/Page column 115.

27
[ 916325-85-4 ]
[ 54998-08-2 ]
5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid [2-amino-4-(4-methyl-piperazin-1-yl)-phenyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃;	A mixture of 5-bromo-lEta-pyrazolo[3,4-b]pyridine-3-carboxylic acid Compound Ic (2.095 g, 8.66 mmol), 4-(4-methyl-piperazin-l-yl)-benzene-r,2-diamine Compound 14a (1.79 g, 8.68 mmol), HATU (3.29 g, 8.66 mmol) and DIPEA (4 mL, 28.7 mmol) in DMF (70 mL) was stirred, at room temperature overnight. The solvent was removed and the residue was purified by silica gel chromatography (10% to 90% of ethyl acetate in hexanes) to yield 5-bromo-lH-pyrazolo[3,4-b]pyridine-3-carboxylic acid [2-amino-4-(4-methyl-piperazin-l-yl)-phenyl]-amide Compound 14b (2 g, 54% yield) as a brown powder. 1H NMR (300 MHz, CD3OD) delta 8.81 (d, IH, 7 = 2.1 Hz), 8.66 (d, IH, 7= 2.1 Hz), 7.42 (d, IH, 7 = 8.7 Hz), 7.11 (dd, IH, 7 = 2.7, 8.7 Hz), 7.03 (d, IH, 7 = 2.7 Hz), 3.92 (b, 2H), 3.65 (b, 2H), 3.31 (b, 2H), 3.16 (b, 2H), 2.81 (s, 3H); MS (ESI) m/z: 431 (M+H+).

References: [1]Patent: WO2006/130673,2006,A1 .Location in patent: Page/Page column 110.

28
[ 916325-85-4 ]
[ 102-51-2 ]
5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (2-amino-5-methoxy-phenyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 45℃;	A mixture of S-bromo-lEta-pyrazoloCS^-bjpyridine-S-carboxylic acidCompound Ic (200 mg, 0.826 mmol), 4-methoxy-benzehe-l,2-diamine Compound 19a (114 mg, 0.826 mmol), EtaATU (314 mg, 0.826 mmol) and DIPEA (213 mg, 1.652 mmol) in DMF (10 mL) was stirred and heated to 45 C overnight. The mixture was diluted with AeOEt (60 mL) and washed with water. The organic layer was separated, dried and evaporated to give a brown solid residue. The residue was recrystallized with AcOEt/hexane mixture to give 5-bromo-lEta-pyrazolo[3,4-b]pyridine-3-carboxylic acid (2-amin-5-methoxy-phenyl)-amide Compound 19b (221 mg, 74% yield) as a light brown powder. MS m/z 362 (M+).

References: [1]Patent: WO2006/130673,2006,A1 .Location in patent: Page/Page column 122.

29
[ 916325-85-4 ]
[ 916326-41-5 ]
[ 916326-42-6 ]

Yield	Reaction Conditions	Operation in experiment
61%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃;	Compound Ic (1.0 g, 4.13 mrnol) and 3-(t°7?-butyl-dimethyl-si]anyloxymethyl)- benzene-l,2-diamine Compound 6a (1.05 g, 4.17 mmol), HATU (1.58 g, 4.16 mmol) EPO <DP n="92"/>and DIPEA (2.5 mL, 35.9 mmol) in DMF (50 mL) was stirred at room temperature overnight. The solvent was removed and the residue was dissolved in ethyl acetate (100 mL), then sequentially washed with hydrochloric acid (20 mL, IM), water (30 mL x 3) and brine (20 mL). The organic solution was evaporated to dryness, in vacuo and purified by silica gel chromatography (10% to 50% of ethyl acetate in hexanes) to yield 5-bromo-lH-pyrazolo[3,4-b]pyridine-3-carboxylic acid [2-amino-3-(tert-butyl- dimethyl-silanyloxymethyl)-phenyl]-amide Compound 6b (1.21g, 61% yield) as a yellow powder. 1H NMR (300 MHz, CDCl3) delta 8.91 (d, IH, J = 2.1 Hz), 8.73 (s, IH), 8.67 (d, IH, 7 = 2.1 Hz), 7.47 (d, IH, 7 = 7.2 Hz), 7.01 (d, IH, 7 = 7.2 Hz), 6.83 (t, IH, J = 7.2 Hz), 4.78 (s, 2H), 0.95 (s, 9H), 0.11 (s, 6H); MS (ESI) m/z: 477 (M+H+).

References: [1]Patent: WO2006/130673,2006,A1 .Location in patent: Page/Page column 90-91.

30
[ 916325-85-4 ]
[ 916325-86-5 ]
N-[2-amino-3-(methoxymethyl)phenyl]-5-bromo-1H-pyrazolo[3,4-b]pyridin-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃;	Compound Ic (1.425 g, 5.89 mmol), Compound Ie (0.896 g, 5.89 mmol), HATU (2.686 g, 7.07 mmol) and DIPEA (3.69 mL, 21.2 mmol) in DMF (15 mL) was stirred at, room temperature overnight. The mixture was then evaporated in vacuo and . purified via chromatography on silica gel with a 10-20% MeOH/methylene chloride gradient to give Compound If 1.265 g (57%). 1H NMR (300 MHz, (CD3)2SO) delta 9.9 (s, br, IH), 8.72 (s, IH), 8.65 (s, IH), 7.25 (d, IH), 7.0 (d, IH), 6.62 (t, IH), 4.7 (s, br, 2H), 4.40 (s, 2H), 3.30 (s, 3H); MS (ESI) m/z: 377 (M+H+), 399 (M+Na+).

References: [1]Patent: WO2006/130673,2006,A1 .Location in patent: Page/Page column 75.

31
[ 916325-85-4 ]
[ 916327-19-0 ]
[ 916327-20-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃;	A mixture of 5-bromo-lH-pyrazolo[3,4-b]pyridine-3-carboxylic acidCompound Ic (0.72 g, 2.05 mmol), Compound 18c (0.58 g, 2.05 mmol), HATU (0.78 g, 2.05 mmol) and DIPEA (1.1 mL, 6.15 mmol) in DMF (30 mL) was stirred at room temperature overnight. The solvent was removed in vacuo and the resulting yellow residue was mixed with AcOEt, sequentially washed with saturated aqueous NH4Cl, 0 IM HCl, H2O and saturated aqueous NaHCO3 and dried over Na2SO4. The solvent was , ' " evaporated to dryness to provide 5-bromo-lH-pyrazolo[3,4-b]pyridine-3-carboxylic acid { 2-amino-4-[2-(tert-butyl-dimethyl-silanyl)-ethoxy] -phenyl } -amide Compound 18d (1.02 g, 98% yield) as a reddish solid. LCMS major peak, 3.523 min, MS (ESI) , m/z 506.1 (M+)/507.1 (M+H+).

References: [1]Patent: WO2006/130673,2006,A1 .Location in patent: Page/Page column 119.

32
[ 916325-85-4 ]
[ 1346169-41-2 ]

References: [1]Inorganic Chemistry,2011,vol. 50,p. 11715 - 11728.

33
[ 916325-85-4 ]
N-[2-amino-3-(methoxymethyl)phenyl]-5-bromo-1H-pyrazolo[3,4-b]pyridin-3-carboxamide [ No CAS ]

References: [1]Inorganic Chemistry,2011,vol. 50,p. 11715 - 11728.

34
[ 916325-85-4 ]
3-(1H-benzimidazol-2-yl)-5-bromo-1H-pyrazolo[3,4-b]pyridine [ No CAS ]

References: [1]Inorganic Chemistry,2011,vol. 50,p. 11715 - 11728.

35
[ 916325-85-4 ]
[ 530-62-1 ]
[ 1346169-39-8 ]

References: [1]Inorganic Chemistry,2011,vol. 50,p. 11715 - 11728.

36
5-bromo-3-methyl-1H-pyrazolo[3,4-b]pyridine [ No CAS ]
[ 916325-85-4 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of NaOH (27 Kg, 675 mol) in water (617 L) was added 5-bromo-3-methyl-1H-pyrazolo[3,4-b]pyridine (XXI) (9.8 Kg, 46.2 mol). The solution was heated at 90 C. for 3 hours under nitrogen before adding a solution of KMnO4 (53.6 Kg, 339 mol) in water (870 L) slowly over 2 hours. The reaction was heated at 95 C. for 5 hours under nitrogen. The solution was cooled to 75 C. and filtered through diatomaceous earth (11 Kg) followed by washing the diatomaceous earth with water (150 L) heated at 75 C. The solution was cooled to 0 C. under nitrogen before the pH was adjusted to 1 with aqueous 35% HCl (75 L). The solution was warmed to room temperature before adding n-BuOH (473 L) which was stirred for 25 min and then the organic layer was separated. n-BuOH (473 L) was again added to the aqueous layer, stirred for 25 min and separated. The combined organic phases were concentrated under vacuum to a volume of 54 L. The n-BuOH was removed by adding to the solution 9×n-heptane (78 L) dropwise over 1 hour and then concentrating the volume to 54 L after each addition of n-heptane. The solid was filtered and washed 3×n-heptane (17 L). The solid was dried under vacuum at 45 C. to give 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XVIII) (3.2 Kg, 13.2 mol, 64.4% purity, 29.0% assay yield). 1H NMR (DMSO-d6, 400 MHz) delta ppm 8.57 (d, J=2.4 Hz, 1H), 8.71 (d, J=2 Hz, 1H), 13.45 (brs, 1H), 14.65 (s, 1H); ESIMS found C7H4BrN3O2 m/z 243.8 (M+H).
		To a solution of NaOH (27 Kg, 675 mol) in water (617 L) was added 5-bromo- 3-methyl-1H-pyrazolo[3,4-b]pyridine (XXXIII) (9.8 Kg, 46.2 mol). The solution was heated at 90oC for 3 hours under nitrogen before adding a solution of KMnO4 (53.6 Kg, 339 mol) in water (870 L) slowly over 2 hours. The reaction was heated at 95oC for 5 hours under nitrogen. The solution was cooled to 75oC and filtered through diatomaceous earth (11 Kg) followed by washing the diatomaceous earth with water (150 L) heated at 75oC. The solution was cooled to 0oC under nitrogen before the pH was adjusted to 1 with aqueous 35% HCl (~75 L). The solution was warmed to room temperature before adding n-BuOH (473 L) which was stirred for 25 min and then the organic layer was separated. n-BuOH (473 L) was again added to the aqueous layer, stirred for 25 min and separated. The combined organic phases were concentrated under vacuum to a volume of ~54 L. The n-BuOH was removed by adding to the solution 9 x n-heptane (78 L) dropwise over 1 hour and then concentrating the volume to ~54 L after each addition of n-heptane. The solid was filtered and washed 3 x n-heptane (17 L). The solid was dried under vacuum at 45oC to give 5- bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XXXIV) (3.2 Kg, 13.2 mol, 64.4% purity, 29.0% assay yield).1H NMR (DMSO-d6, 400 MHz) d ppm 8.57 (d, J=2.4Hz, 1H), 8.71 (d, J=2Hz, 1H), 13.45 (brs, 1H), 14.65 (s, 1H); ESIMS found C7H4BrN3O2 m/z 243.8 (M+H).

References: [1]Inorganic Chemistry,2011,vol. 50,p. 11715 - 11728.
[2]Patent: US2013/296302,2013,A1 .Location in patent: Paragraph 0507.
[3]Patent: WO2019/241540,2019,A1 .Location in patent: Paragraph 0341; 0345.

37
[ 116834-96-9 ]
[ 916325-85-4 ]

References: [1]Inorganic Chemistry,2011,vol. 50,p. 11715 - 11728.
[2]Patent: WO2011/84486,2011,A1 .
[3]Patent: US2013/296302,2013,A1 .
[4]Patent: US2013/296302,2013,A1 .
[5]Patent: US2016/68550,2016,A1 .
[6]Patent: WO2016/40193,2016,A1 .
[7]Patent: WO2019/241540,2019,A1 .

38
[ 916325-85-4 ]
[ 6638-79-5 ]
[ 1314734-57-0 ]

Yield	Reaction Conditions	Operation in experiment
92%		Step 8[00182] To a solution of 5-bromo-lH-pyrazole[3,4-£]pyridine-3-carboxylic acid (VIII) (0.242 g, 1 mmol) in dry DMF (5 mL) was added CDI (0.178 g, 1.1 mmol) and heated for 3 h at 65C under nitrogen. The solution was cooled to room temperature and Nu,Omicron-dimethyl hydroxylamine hydrochloride (0.107 g, 1.1 mmol) was added to the solution. The solution was again heated for 3 h at 65C under nitrogen. The solution was cooled and the solvent was evaporated under reduced pressure. The residue was dissolved in DCM, washed successively with a 10% HC1 solution, a saturated NaHC03 solution and brine. The organic phase was dried over MgS04, filtered and concentrated under reduced pressure to produce 5-bromo-N-methoxy-N-methyl-lH-pyrazolo[3,4- £]pyridine-3-carboxamide (IX) as a white solid (260 mg, 0.91 mmol, 92%> yield). 1H NMR (CDC13) delta ppm 3.55 (s, 3H), 3.78 (s, 3H), 8.59 (d, J=3.01 Hz, 1 H), 8.67 (d, J=3.01 Hz, 1 H); ESIMS found for C9H9BrN402 mlz 285.4 (M+H).
92%		To a solution of 5-bromo-1H-pyrazole[3,4-b]pyridine-3-carboxylic acid (XVIII) (0.242 g, 1 mmol) in dry DMF (5 mL) was added CDI (0.178 g, 1.1 mmol) and heated for 3 h at 65 C. under nitrogen. The solution was cooled to room temperature and N,O-dimethyl hydroxylamine hydrochloride (0.107 g, 1.1 mmol) was added to the solution. The solution was again heated for 3 h at 65 C. under nitrogen. The solution was cooled and the solvent was evaporated under reduced pressure. The residue was dissolved in DCM, washed successively with a 10% HCl solution, a saturated aqueous NaHCO3 solution and brine. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to produce 5-bromo-N-methoxy-N-methyl-1H-pyrazolo[3,4-b]pyridine-3-carboxamide (XIX) as a white solid (260 mg, 0.91 mmol, 92% yield). 1H NMR (CDCl3) delta ppm 3.55 (s, 3H), 3.78 (s, 3H), 8.59 (d, J=3.01 Hz, 1H), 8.67 (d, J=3.01 Hz, 1H); ESIMS found for C9H9BrN4O2 m/z 285.4 (M+H).
92%		Step 8 To a solution of 5-bromo-1H-pyrazole[3,4-b]pyridine-3-carboxylic acid (XVI) (0.242 g, 1 mmol) in dry DMF (5 mL) was added CDI (0.178 g, 1.1 mmol) and heated for 3 h at 65 C. under nitrogen. The solution was cooled to room temperature and N,O-dimethyl hydroxylamine hydrochloride (0.107 g, 1.1 mmol) was added to the solution. The solution was again heated for 3 h at 65 C. under nitrogen. The solution was cooled and the solvent was evaporated under reduced pressure. The residue was dissolved in DCM, washed successively with a 10% HCl solution, a saturated aqueous NaHCO3 solution and brine. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to produce 5-bromo-N-methoxy-N-methyl-1H-pyrazolo[3,4-b]pyridine-3-carboxamide (XVII) as a white solid (260 mg, 0.91 mmol, 92% yield). 1H NMR (CDCl3) delta ppm 3.55 (s, 3H), 3.78 (s, 3H), 8.59 (d, J=3.01 Hz, 1H), 8.67 (d, J=3.01 Hz, 1H); ESIMS found for C9H9BrN4O2 m/z 285.4 (M+H).

92%		To a solution of 5-bromo-1H-pyrazole[3,4-b]pyridine-3-carboxylic acid (XVI) (0.242 g, 1 mmol) in dry DMF (5 mL) was added CDI (0.178 g, 1.1 mmol) and heated for 3 h at 65C under nitrogen. The solution was cooled to room temperature and Nu,Omicron-dimethyl hydroxylamine hydrochloride (0.107 g, 1.1 mmol) was added to the solution. The solution was again heated for 3 h at 65C under nitrogen. The solution was cooled and the solvent was evaporated under reduced pressure. The residue was dissolved in DCM, washed successively with a 10%) HCl solution, a saturated aqueous NaHCO3 solution and brine. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to produce 5-bromo-N-methoxy-N-methyl-1H-pyrazolo[3,4-6]pyridine-3-carboxamide (XVII) as a white solid (260 mg, 0.91 mmol, 92% yield). 1H NMR (CDCl3) delta ppm 3.55 (s, 3H), 3.78 (s, 3H), 8.59 (d, J=3.01Hz, 1H), 8.67 (d, J=3.01Hz, 1H); ESIMS found for C9H9BrN4O2 m/z 285.4 (M+H).
7.94 g		<strong>[916325-85-4]5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid</strong> ((III), 7.91 g, 32.7 mmol) and 1,1?- carbonyldiimidazole (5.83 g, 35.9 mmol) were stirred in 200 mL of DMF at 60C for 45 minutes. To the resulting suspension was added N,O-dimethylhydroxylamine hydrochloride (3.51 g, 35.9 mmol) and the mixture was stirred for 4 h at 65 C. Most of the solvent was removed under vacuum and to the residue half sat. NaHCO3-solution was added. The solids were collected by suction filtration, washed with water and dried at 110 C. Yield: 7.94 g, HPLC purity: 96 %, 1H NMR (200 MHz, DMSO) delta 14.46 (s, 1H), 8.62 (d, J = 20.4 Hz, 2H), 3.76 (s, 3H), 3.44 (s, 3H), [M-H]- = 283.0 / 285.0.

References: [1]Patent: WO2011/84486,2011,A1 .Location in patent: Page/Page column 106-107; 113.
[2]Patent: US2013/296302,2013,A1 .Location in patent: Paragraph 0500.
[3]Patent: US2016/68550,2016,A1 .Location in patent: Paragraph 1062.
[4]Patent: WO2016/40193,2016,A1 .Location in patent: Paragraph 0709.
[5]Patent: WO2019/149738,2019,A1 .Location in patent: Page/Page column 51; 52.

39
[ 55676-21-6 ]
[ 916325-85-4 ]

References: [1]Patent: WO2011/84486,2011,A1 .
[2]Patent: US2013/296302,2013,A1 .
[3]Patent: US2013/296302,2013,A1 .
[4]Patent: US2016/68550,2016,A1 .
[5]Patent: WO2016/40193,2016,A1 .
[6]Patent: WO2019/241540,2019,A1 .

40
[ 109-09-1 ]
[ 916325-85-4 ]

41
[ 131674-39-0 ]
[ 916325-85-4 ]

Historical Records

Technical Information

• Alkyl Halide Occurrence • Arndt-Eistert Homologation • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hunsdiecker-Borodin Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Carboxylic Acids • Reactions of Dihalides • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Ugi Reaction

Related Functional Groups of
[ 916325-85-4 ]

Bromides

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Carboxylic Acids

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Related Parent Nucleus of
[ 916325-85-4 ]

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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

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CAS No.: 916325-85-4

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CAS No.: 916325-85-4

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[ 916325-85-4 ] Synthesis Path-Downstream 1~41

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[ 916325-85-4 ]

Bromides

Carboxylic Acids

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[ 916325-85-4 ]

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{[proInfo.proName]}

CAS No.: 916325-85-4

{[proInfo.proName]}

CAS No.: 916325-85-4

Alternative Products

Product Details of [ 916325-85-4 ]

Safety of [ 916325-85-4 ]

Computational Chemistry of [ 916325-85-4 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 916325-85-4 ]

[ 916325-85-4 ] Synthesis Path-Downstream 1~41

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of [ 916325-85-4 ]

Bromides

Carboxylic Acids

Related Parent Nucleus of [ 916325-85-4 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

Dissolution Calculator

Related Functional Groups of
[ 916325-85-4 ]

Related Parent Nucleus of
[ 916325-85-4 ]