[ CAS No. 271-47-6 ] {[proInfo.proName]}

Name: 271-47-6|1H-Pyrazolo[3,4-c]pyridine|98%
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Quality Control of [ 271-47-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 271-47-6 ]

CAS No. :	271-47-6	MDL No. :	MFCD00661308
Formula :	C₆H₅N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KNYHISBJRQVMAZ-UHFFFAOYSA-N
M.W :	119.12	Pubchem ID :	6451441
Synonyms :

Calculated chemistry of [ 271-47-6 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	33.89
TPSA :	41.57 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.69 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.57
Log Po/w (XLOGP3) :	0.48
Log Po/w (WLOGP) :	0.96
Log Po/w (MLOGP) :	-0.11
Log Po/w (SILICOS-IT) :	1.67
Consensus Log Po/w :	0.71

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.62
Solubility :	2.85 mg/ml ; 0.0239 mol/l
Class :	Very soluble
Log S (Ali) :	-0.92
Solubility :	14.2 mg/ml ; 0.12 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.49
Solubility :	0.387 mg/ml ; 0.00325 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.42

Safety of [ 271-47-6 ]

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

Application In Synthesis of [ 271-47-6 ]

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

Upstream synthesis route of [ 271-47-6 ]
Downstream synthetic route of [ 271-47-6 ]

[ 271-47-6 ] Synthesis Path-Upstream 1~7

1
[ 23056-47-5 ]
[ 19006-76-9 ]
[ 271-47-6 ]

Reference： [1] Patent: US5300478, 1994, A,

2
[ 462-08-8 ]
[ 271-47-6 ]

Reference： [1] Patent: US5300478, 1994, A,

3
[ 504-29-0 ]
[ 271-47-6 ]

Reference： [1] Patent: US5300478, 1994, A,

4
[ 271-47-6 ]
[ 76006-14-9 ]

5
[ 271-47-6 ]
[ 76006-13-8 ]

Reference： [1] Archiv der Pharmazie, 1989, vol. 322, # 12, p. 885 - 887
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2398 - 2404
[3] Heterocycles, 1999, vol. 51, # 7, p. 1661 - 1667
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2398 - 2404

6
[ 271-47-6 ]
[ 76006-17-2 ]

Reference： [1] Heterocycles, 1999, vol. 51, # 7, p. 1661 - 1667
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2398 - 2404

7
[ 271-47-6 ]
[ 1082040-63-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃;	A suspension of 1H-pyrazolo[3,4-c]pyridine (300 mg, 2.52 mmol, 1.00 equiv), KOH (500 mg,8.91 mmol, 3.50 equiv), and diiodane (1.28 g, 5.04 mmol, 2.00 equiv) in DMF (10 mL) was stirredovernight at room temperature. The reaction was quenched by water, extracted with ethyl acetate,dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified bya silica gel column with ethyl acetate/petroleum ether (1:1) to give the title compound (577 mg,84percent) as a yellow solid. LC-MS (ES, mlz): 246 [M+H].
73%	With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 3 h;	To a solution of 1H-pyrazolo[3,4-c]pyridine (4.0 g, 33.6 mmol, 1.0 eq.) in DMF(40 mL) were added K2C03 (9.3 g, 100.8 mmol, 3.0 eq.), ‘2 (7.9 g, 33.6 mmol, 1.0 eq.). Theresulting mixture was stirred at r.t. for 3 hr, then diluted by H20 and filtered. The collectedsolid was dried to give 3-iodo-1H-pyrazolo[3,4-c]pyridine (6.0 g, 73.0 percent).
73%	With iodine; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3 h;	To a solution of 1H-pyrazolo[3,4-c]pyridine (4.0 g, 33.6 mmol, 1.0 eq.) in DMF (40 mL) were added K2C03 (9.3 g, 100.8 mmol, 3.0 eq.) and ‘2 (7.9 g, 33.6 mmol, 1.0 eq.). The resulting mixture was stirred at rt for 3 h, then diluted by H20 and filtered. The solid was collected and dried to give 3-iodo-1H-pyrazolo[3,4-c]pyridine (6.0 g, 73.0 percent yield).

Reference： [1] Patent: WO2015/25025, 2015, A1, . Location in patent: Page/Page column 357
[2] Patent: WO2017/98328, 2017, A2, . Location in patent: Paragraph 00222
[3] Patent: WO2018/15818, 2018, A2, . Location in patent: Paragraph 00177
[4] Patent: WO2012/93101, 2012, A1, . Location in patent: Page/Page column 152
[5] Patent: WO2014/2053, 2014, A1, . Location in patent: Page/Page column 51
[6] Patent: WO2014/2051, 2014, A2, . Location in patent: Page/Page column 54
[7] Patent: WO2014/2052, 2014, A1, . Location in patent: Page/Page column 49
[8] Patent: WO2014/2058, 2014, A2, . Location in patent: Page/Page column 60
[9] Patent: WO2014/9833, 2014, A2, . Location in patent: Page/Page column 45
[10] Patent: WO2014/2054, 2014, A1, . Location in patent: Page/Page column 63

[ 271-47-6 ] Synthesis Path-Downstream 1~54

1
[ 271-47-6 ]
[ 76006-14-9 ]

Reference： [1]Archiv der Pharmazie,1989,vol. 322,p. 885 - 887
[2]Journal of the Chemical Society. Perkin transactions I,1980,p. 2398 - 2404
[3]Heterocycles,1999,vol. 51,p. 1661 - 1667

2
[ 271-47-6 ]
[ 76006-13-8 ]

Reference： [1]Archiv der Pharmazie,1989,vol. 322,p. 885 - 887
[2]Journal of the Chemical Society. Perkin transactions I,1980,p. 2398 - 2404
[3]Heterocycles,1999,vol. 51,p. 1661 - 1667
[4]Journal of the Chemical Society. Perkin transactions I,1980,p. 2398 - 2404

3
[ 271-47-6 ]
[ 76006-15-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2398 - 2404
[2]Heterocycles,1999,vol. 51,p. 1661 - 1667

5
[ 1001013-86-0 ]
[ 271-47-6 ]
C₂₆H₁₉N₇ [ No CAS ]
1-(4-(1-(6-methylpyridin-3-yl)-4-(pyridin-2-yl)-1H-imidazol-2-yl)phenyl)-1H-pyrazolo[3,4-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;copper(l) iodide; trans-N,N-dimethyl-cyclohexane-1,2-diamine; In 1,4-dioxane; at 150℃; for 3h;Microwave irradiation;	Example 56; 1.f4-f1-(6-methvipyridin-3-yl)-4-rpyridin-2-v»-1H-imidazol-2-ylbhenylV1H-pyrazolor3.4- clpvridine; A mixture of 2-(2-(4-iodophenyl)-1-(6-methylpyridin-3-yl)-1H-imidazol-4-yl)pyridine (175 mg, 0.40 mmol), 1 H-pyrazoIo[3,4-c]pyridine (J. Chem. Soc. Perkin Transactions I1 1973, p. 2901, 0.48 mg, 0.40 mmol), CuI (3.8 mg, 0.020 mmol), K3PO4 (178 mg, 0.84 mmol) andN,N-dimethyl-frans-1,2-cyclohexanediamine (12 mg, 0.080 mmol) in p-dioxane (1 ml_) was heated by microwave at 150 0C for 3h, filtered through silica using DCM-MeOH1 and concentrated and the residue purified by SGC (1% MeOH in DCM, 0.5 % NH4OH) giving a yellow solid. Yield 45 mg, 26%. 1H NMR (CDCI3) showed a 10:1 mixture of two substances which were not resolved by HPLCMS (4.23 min, m/e 430 (MH+). For the major substance.59.28 (s, 1H)1 8.60 (d, 1H, J = 5 Hz), 8.53 (d, 1H, J = 2.5 Hz), 8.41 (d, 1H1 J = 5 Hz)1 8.32 (br,1H), 8.26 (S1 1H), 7.96 (br, 1H), 7.76 (m, 2H), 7.71 <m, 1H), 7.66 (m, 2H), 7.55 (m, 1H), 7.34 <n="132"/>(br, 1H)1 7.26-7.24 (m, 2H)1 2.64 (s, 3H). For the minor substance (partial) 9.25 (s, 1H), 2.67 (S1 3H). IC50 = 6.44 nM

Reference： [1]Patent: WO2008/4117,2008,A1 .Location in patent: Page/Page column 130-131

6
[ 271-47-6 ]
[ 76006-17-2 ]

Reference： [1]Heterocycles,1999,vol. 51,p. 1661 - 1667
[2]Journal of the Chemical Society. Perkin transactions I,1980,p. 2398 - 2404

7
[ 271-47-6 ]
3-cyano-1H-pyrazolo[3,4-c]pyridine [ No CAS ]

Reference： [1]Heterocycles,1999,vol. 51,p. 1661 - 1667

8
[ 271-47-6 ]
1<i>H</i>-pyrazolo[3,4-<i>c</i>]pyridine-3-diazonium; hydroxide [ No CAS ]

Reference： [1]Heterocycles,1999,vol. 51,p. 1661 - 1667

9
[ 271-47-6 ]
[ 76006-18-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2398 - 2404

10
[ 271-47-6 ]
[ 76006-22-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2398 - 2404

11
[ 271-47-6 ]
[ 76006-24-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2398 - 2404

12
[ 271-47-6 ]
[ 76006-23-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2398 - 2404

13
[ 23056-47-5 ]
[ 19006-76-9 ]
[ 271-47-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; ethanethiol; In N,N-dimethyl-formamide;	B. Preparation of 5-ethanethio (or sulfonyl) - pyrazolo [3,4-c]pyridine STR23 A solution of 8 g <strong>[23056-47-5]2-<strong>[23056-47-5]bromo-4-methyl-5-nitropyridine</strong></strong> 6.7 g potassium carbonate and 3.4 g ethanethiol in dimethyl formamide was heated to 70 C. for 6 hours. The solution was washed, dried and reduced under vacuum. Yield, 8 g of ethanethiopyridine as an oil.

Reference： [1]Patent: US5300478,1994,A

14
[ 462-08-8 ]
[ 271-47-6 ]

Yield	Reaction Conditions	Operation in experiment
		The above 5-amino pyridine was reacted as in Example 1 to give the pyrazolo [3,4-c]pyridine, then the 1-N-arylpyrazolo [3,4-c]pyridine (Compound No. 25). The 1-aryl-5-ethanethiopyrazolo [3,4-c]pyridine can be oxidized in cold (0 C.) methylene chloride with 2.1 g meta-chloroperoxybenzoic acid, as previously described.

Reference： [1]Patent: US5300478,1994,A

15
[ 504-29-0 ]
[ 271-47-6 ]

Yield	Reaction Conditions	Operation in experiment
		Pyrazolo [3,4-c]pyridine Using the precedures described in Example 2, the corresponding amino-pyridine was reacted to form the pyrazolo [3,4-c]pyridine and the 1-aryl-pyrazolo [3,4-c]pyridine (Compound No. 23).

Reference： [1]Patent: US5300478,1994,A

16
[ 271-47-6 ]
[ 1082040-63-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃;	A suspension of 1H-pyrazolo[3,4-c]pyridine (300 mg, 2.52 mmol, 1.00 equiv), KOH (500 mg,8.91 mmol, 3.50 equiv), and diiodane (1.28 g, 5.04 mmol, 2.00 equiv) in DMF (10 mL) was stirredovernight at room temperature. The reaction was quenched by water, extracted with ethyl acetate,dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified bya silica gel column with ethyl acetate/petroleum ether (1:1) to give the title compound (577 mg,84%) as a yellow solid. LC-MS (ES, mlz): 246 [M+H].
73%	With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 3h;	To a solution of 1H-pyrazolo[3,4-c]pyridine (4.0 g, 33.6 mmol, 1.0 eq.) in DMF(40 mL) were added K2C03 (9.3 g, 100.8 mmol, 3.0 eq.), ?2 (7.9 g, 33.6 mmol, 1.0 eq.). Theresulting mixture was stirred at r.t. for 3 hr, then diluted by H20 and filtered. The collectedsolid was dried to give 3-iodo-1H-pyrazolo[3,4-c]pyridine (6.0 g, 73.0 %).
73%	With iodine; potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3h;	To a solution of 1H-pyrazolo[3,4-c]pyridine (4.0 g, 33.6 mmol, 1.0 eq.) in DMF (40 mL) were added K2C03 (9.3 g, 100.8 mmol, 3.0 eq.) and ?2 (7.9 g, 33.6 mmol, 1.0 eq.). The resulting mixture was stirred at rt for 3 h, then diluted by H20 and filtered. The solid was collected and dried to give 3-iodo-1H-pyrazolo[3,4-c]pyridine (6.0 g, 73.0 % yield).

73%	With iodine; potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3h;	To a solution of lH-pyrazolo[3,4-c]pyridine (4.0 g, 33.6 mmol, 1.0 eq.) in DMF (40 mL) were added K2C03 (9.3 g, 100.8 mmol, 3.0 eq.), I2 (7.9 g, 33.6 mmol, 1.0 eq.). The resulting mixture was stirred at r.t. for 3 hr, then diluted by H20 and filtered. The collected solid was dried to give 3-iodo-lH- pyrazolo[3,4-c]pyridine (6.0 g, 73.0 % yield).
	With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 16h;	To a solution of 1 H-pyrazolo[3,4-c]pyridine [271-47-6 ] (4.00 g, 33.6 mmol) in DMF (50 mL) were added iodine (12.8 g, 50.4 mmol) and potassium hydroxide (4.70 g, 84.0 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was diluted with 10% sodium thiosulfate and water, then extracted (3x) with EtOAc. The combined organic extracts were washed with brine, then dried (Phase separator) and concentrated under vacuum. MS (LC/MS): 246.0 [M+H]+; tR (HPLC conditions k): 0.48 min.
	With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 16h;	A. 3-Iodo-I H-pyrazolo[3,4-c]pyridineTo a solution of 1 H-pyrazolo[3,4-c]pyridine [27 1-47-6 1(4.00 g, 33.6 mmol) in DMF (50 mL) were added iodine (12.8 g, 50.4 mmol) and potassium hydroxide (4.70 g, 84.0 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was diluted with 10% sodium thiosulfate and water, then extracted (3x) with EtOAc. The combined organic extracts were washed with brine, dried (Phase separator) and concentrated under vacuum. MS (LCMS): 246.0 [M+H]+; tR (HPLC conditions d): 0.48 mm.
	With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 16h;	A. 3-lodo-1 H-pyrazolo[3,4-c]pyridineTo a solution of IH-pyrazolo[3,4-c]pyridine [271-47-6 ] (4.00 g, 33.6 mmol) in DMF (50 mL) were added iodine (12.8 g, 50.4 mmol) and potassium hydroxide (4.70 g, 84.0 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was diluted with 10% sodium thiosulfate and water, then extracted (3x) with EtOAc. The combined organic extracts were washed with brine, dried (phase separator) and concentrated. MS (LC/MS): 246.0 [M+H]+; tR (H PLC conditions d): 0.48 mm.
	With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 16h;	To a solution of 1 H-pyrazolo[3,4-c]pyridine [271-47-6 ] (4.00 g, 33.6 mmol) in DMF (50 mL) were added iodine (12.8 g, 50.4 mmol) and potassium hydroxide (4.70 g, 84.0 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was diluted with 10% sodium thiosulfate and water, then extracted (3x) with EtOAc. The combined organic extracts were washed with brine, dried (Phase separator) and concentrated under vacuum. MS (LC/MS): 246.0 [M+H]+; tR (HPLC conditions d): 0.48 min.
	With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 16h;	To a solution of 1H-pyrazolo[3,4-c]pyridine [271-47-6] (4.00 g, 33.6 mmol) in DMF (50 mL) were added iodine (12.8 g, 50.4 mmol) and potassium hydroxide (4.70 g, 84.0 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was diluted with 10% sodium thiosulfate and water and extracted with EtOAc (3x). The combined organic extracts were washed with brine, dried (phase separator) and concentrated to afford the title compound. MS (LCMS): 246.0 [M+H]+; tR (H PLC conditions d): 0.48 mm.
	With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 16h;Inert atmosphere;	To a solution of 1H-pyrazolo[3,4-c]pyridine [271-47-6 1(4.00 g, 33.6 mmol) in DMF (50 mL) were added iodine (12.8 g, 50.4 mmol) and potassium hydroxide (4.70 g, 84.0 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was diluted with 10% sodium thiosulfate and water, then extracted (3x) with EtOAc. The combined organic extracts were washed with brine, dried (Phase separator) and concentrated under vacuum. MS (LCMS):246.0 [M+H]+; tR (H PLC conditions b): 0.48 mm.
	With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 16h;	To a solution of 1H-pyrazolo[3,4-c]pyridine [271-47-61(4.00 g, 33.6 mmol) in DMF (50 mL) were added iodine (12.8 g, 50.4 mmol) and potassium hydroxide (4.70 g, 84.0 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was diluted with 10% sodium thiosulfate and water, then extracted with EtOAc (3x). The combined organic extracts were washed with brine, dried (phase separator) and concentrated. MS (LCMS): 246.0 [M+H]+; tR (H PLC conditions d):0.48 mm.

Reference： [1]Patent: WO2015/25025,2015,A1 .Location in patent: Page/Page column 357
[2]Patent: WO2017/98328,2017,A2 .Location in patent: Paragraph 00222
[3]Patent: WO2018/15818,2018,A2 .Location in patent: Paragraph 00177
[4]Patent: WO2018/229543,2018,A2 .Location in patent: Paragraph 00192
[5]Patent: WO2012/93101,2012,A1 .Location in patent: Page/Page column 152
[6]Patent: WO2014/2053,2014,A1 .Location in patent: Page/Page column 51
[7]Patent: WO2014/2051,2014,A2 .Location in patent: Page/Page column 54
[8]Patent: WO2014/2052,2014,A1 .Location in patent: Page/Page column 49
[9]Patent: WO2014/2058,2014,A2 .Location in patent: Page/Page column 60
[10]Patent: WO2014/9833,2014,A2 .Location in patent: Page/Page column 45
[11]Patent: WO2014/2054,2014,A1 .Location in patent: Page/Page column 63

17
[ 271-47-6 ]
[ 1386457-65-3 ]

Reference： [1]Patent: WO2012/93101,2012,A1
[2]Patent: WO2014/2053,2014,A1
[3]Patent: WO2014/2051,2014,A2
[4]Patent: WO2014/2052,2014,A1
[5]Patent: WO2014/2058,2014,A2
[6]Patent: WO2014/9833,2014,A2
[7]Patent: WO2014/2054,2014,A1
[8]Patent: WO2017/98328,2017,A2
[9]Patent: WO2018/15818,2018,A2

18
[ 271-47-6 ]
[ 1386457-66-4 ]

19
[ 271-47-6 ]
[ 1386457-68-6 ]

Reference： [1]Patent: WO2012/93101,2012,A1
[2]Patent: WO2014/2051,2014,A2
[3]Patent: WO2014/2052,2014,A1
[4]Patent: WO2014/2058,2014,A2
[5]Patent: WO2014/9833,2014,A2
[6]Patent: WO2014/2054,2014,A1

20
[ 271-47-6 ]
[ 1386457-67-5 ]

Reference： [1]Patent: WO2012/93101,2012,A1
[2]Patent: WO2012/93101,2012,A1
[3]Patent: WO2014/2053,2014,A1
[4]Patent: WO2014/2051,2014,A2
[5]Patent: WO2014/2051,2014,A2
[6]Patent: WO2014/2052,2014,A1
[7]Patent: WO2014/2052,2014,A1
[8]Patent: WO2014/2058,2014,A2
[9]Patent: WO2014/2058,2014,A2
[10]Patent: WO2014/9833,2014,A2
[11]Patent: WO2014/9833,2014,A2
[12]Patent: WO2014/2054,2014,A1
[13]Patent: WO2017/98328,2017,A2
[14]Patent: WO2018/15818,2018,A2
[15]Patent: WO2018/229543,2018,A2

21
[ 271-47-6 ]
[ 1330064-36-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1989 - 1992

22
[ 271-47-6 ]
[ 1330064-73-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1989 - 1992

23
[ 271-47-6 ]
[ 350-46-9 ]
[ 1330064-77-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1989 - 1992

24
[ 271-47-6 ]
[ 1528560-45-3 ]

Reference： [1]Patent: WO2014/2054,2014,A1

25
bis-(((isopropyl)sulfinyl)oxy)zinc [ No CAS ]
[ 271-47-6 ]
C₉H₁₁N₃ [ No CAS ]

Reference： [1]RSC Advances,2014,vol. 4,p. 17262 - 17264

26
[ 271-47-6 ]
[ 1430063-99-2 ]
C₂₇H₃₅F₂N₃O₂ [ No CAS ]
C₂₇H₃₅F₂N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; at 20℃; for 15h;	To a suspension of K2CO3(55mg, 0.4mmol) in THF (5mL) was added <strong>[271-47-6]2H-<strong>[271-47-6]pyrazolo[3,4-c]pyridine</strong></strong> (48mg, 0.4mmol) and 10 (86 mg, 0.2mmol). The mixture was stirred at RT for 15h. The residue mixture was poured into 5mL H20 and extracted with EtOAc (2 x 10 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue mixture was purified by reverse-phase prep-HPLC to afford SA-99 as a white solid (4mg, 4% ) and SA-100 as a white solid (19mg, 20% ) and a white solid byproduct (4mg, 4% ). Compound SA-99: 1H NMR (500 MHz, CDC13) delta (ppm): 9.25 (s, 1H), 8.17 (d, 1H), 7.53 (dd, 1H), 5.87 (t, 1H), 5.32 (AB, 1H), 5.23 (AB, 1H), 2.68 (t, 1H), 2.27-2.20 (m, 1H), 0.73 (s, 3H). LC-MS: rt =2.12 mm, m/z = 472.0 [M+H]+Compound SA-100: 1H NMR (500 MHz, CDC13) delta (ppm): 8.80 (s, 1H), 8.33 (d, 1H), 8.10 (s, 1H), 7.65 (dd, 1H), 5.87 (t, 1H), 5.28 (AB, 1H), 5.23 (AB, 1H), 2.69 (t, 1H), 2.24-2.13 (m, 2H), 0.73 (s, 3H). LC-MS: rt = 2.18 mm, m/z = 472.0 [M+H]+

Reference： [1]Patent: WO2014/169832,2014,A1 .Location in patent: Page/Page column 136

27
[ 1430064-09-7 ]
[ 271-47-6 ]
C₂₈H₃₉N₃O₃ [ No CAS ]
C₂₈H₃₉N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; at 20℃; for 15h;	To a suspension of K2CO3(55mg, 0.4mmol) in THF (5mL) was added 3H-pyrazolo[3,4-c]pyridine (47.6mg, 0.4mmol) and 10 (85 mg, 0.2mmol). The mixture was stirred at RT for 15h then was poured into 5mL H20 and extracted with EtOAc (2 x 10 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue mixture was purified by reverse-phase prep-HPLC to afford SA-118 as a white solid (21mg,22.5% ) and SA- 119 as a white solid (15mg, 16.1%). Compound SA-118: 1H NMR (500 MHz, CDC13) delta (ppm): 9.25 (s, 1H) , 8.16 (d, 1H), 7.98 (s, 1H), 7.52 (dd, 1H), 5.32 (AB, 1H), 5.23 (AB, 1H), 3.42 (AB, 1H), 3.39 (AB, 1H), 3.40 (s, 3H), 2.67 (t, 1H), 2.26-2.19 (m, 1H), 2.14-2.12 (m, 1H), 0.71 (s, 3H). LC-MS: rt = 2.11 mm, m/z = 466.1 [M+H]+Compound SA-119: 1H NMR (500 MHz, CDC13) delta (ppm): 8.79 (s, 1H), 8.33 (d, 1H), 8.09 (s, 1H), 7.64 (d, 1H), 5.28 (AB, 1H), 5.23 (AB, 1H), 3.43 (AB, 1H), 3.40 (s, 3H), 3.39 (AB, 1H), 2.71-2.67 (m, 1H), 2.21-2.12 (m, 1H), 0.72 (s, 3H). LC- MS: rt = 2.18 mm, m/z = 466.1 [M+H]+

Reference： [1]Patent: WO2014/169832,2014,A1 .Location in patent: Page/Page column 148; 149

28
C₂₁H₃₂BrFO₂ [ No CAS ]
[ 271-47-6 ]
C₂₇H₃₆FN₃O₂ [ No CAS ]
C₂₇H₃₆FN₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; at 50℃; for 2h;	To a solution of crude reactant SG (246.9 mg, 0.595 mmol, theoretical amount) in anhydrous THF (5 mL) was added lH-pyrazolo[3,4-c]pyridine (142 mg, 1.188 mmol) followed by potassium carbonate (164 mg, 1.188 mmol). The solution was heated at 50 C for 2 hours. Then the solution was diluted with ethyl acetate (200 mL). The resulting solution was washed with brine (2x100 mL), dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by reverse phase prep-HPLC to afford fraction 1 and 2. Fraction 1 was pure product SB-18 (11.5 mg, 0.0254 mmol, Yield=4.3% (2 steps)). But fraction 2 was impure and crude product was further purified by silica gel chromatography (eluant: petroleum ether / ethyl acetate = 1 : 1) to afford pure product SB-19 (13.9 mg, 0.0306 mmol, Yield=5.2% (2 steps)). Both products were white solid. SB-18: 1H NMR (400 MHz, CDC13) 5(ppm): 9.26 (IH, s), 8.17 (IH, d), 7.98 (IH, s), 7.53 (IH, dd), 5.32 (IH, AB), 5.23 (IH, AB), 4.17 (2H, d), 2.69 (IH, t), 0.73 (3H, s). LCMS: rt = 2.10 mm, m/z = 454.1 [M+H]+SB-19: 1H NMR (400 MHz, CDC13) 5(ppm): 8.80 (IH, s), 8.34 (IH, d), 8.10 (IH, s), 7.64 (IH, d), 5.27 (IH, AB), 5.25 (IH, AB), 4.18 (IH, d), 2.70 (IH, t), 0.74 (3H, s). LCMS: rt = 2.26 mm, m/z = 454.2 [M+H]+

Reference： [1]Patent: WO2014/169832,2014,A1 .Location in patent: Page/Page column 165; 166

29
C₂₂H₃₅BrO₂ [ No CAS ]
[ 271-47-6 ]
C₂₈H₃₉N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; at 60℃; for 2h;	To a solution of crude reactant SH (100 mg, 0.241 mmol) in anhydrous THF (5 mL) was added 2H-pyrazolo[3,4-c]pyridine (143mg, 1.2mmol) followed by potassium carbonate (170g, 1.2 mmol). The solution was heated at 60 C for 2h, then the solution was cooled to room temperature and diluted with ethyl acetate (100 mL). The resulting solution was washed with brine (2x50 mL), dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by reverse phase prep-HPLC to afford product SB-32 (11 mg, 0.09 mmol, Yield=8.3%) as white solid. SB-32: 1H NMR (500 MHz, CDC13) 5(ppm): 8.80(1H, s),8.33(lH, d), 8.10(1H, s),7.67(lH, d), 5.27(1H,AB), 5.25(lH,AB),2.70(lH,t), 1.45-1.51(2H,q), 0.91 (3H, t), 0.73 (3H, s). LCMS:rt=2.46min, m/z=450 [M+H]+

Reference： [1]Patent: WO2014/169832,2014,A1 .Location in patent: Page/Page column 171; 172

30
[ 1430063-79-8 ]
[ 271-47-6 ]
C₂₈H₃₉N₃O₃ [ No CAS ]
C₂₈H₃₉N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; at 50℃; for 2h;	To a solution of crude reactant SI (245.3 mg, 0.573 mmol, theoretical amount) in anhydrous THF (5 mL) was added lH-pyrazolo[3,4-c]pyridine (137 mg, 1.148 mmol) followed by potassium carbonate (159 mg, 1.148 mmol). The solution was heated at 50 C for 2 hours, then the solution was diluted with ethyl acetate (200 mL). The resulting solution was washed with brine (2x100 mL), dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by reverse phase prep-HPLC to afford product SB-45 (5 mg, 0.011 mmol, Yield=1.9% (2 steps)) and product SB-46 (21.7 mg, 0.0466 mmol, Yield=8.2% (2 steps)) as a white solid. Compound SB- 45: 1H NMR (400 MHz, CDC13) 5(ppm): 9.26 (IH, s), 8.17 (IH, d), 7.99 (IH, s), 7.53 (IH, d), 5.32 (IH, AB), 5.24 (IH, AB), 3.39 (3H, s), 3.20 (2H, s), 2.69 (IH, t), 0.72 (3H, s). LC-MS: rt = 2.22 mm, m/z = 466.2 [M+H]+Compound SB-46: 1H NMR (400 MHz, CDC13) 5(ppm): 8.80 (IH, s), 8.34 (IH, d), 8.10 (IH, s), 7.65 (IH, dd), 5.27 (IH, AB), 5.25 (IH, AB), 3.40 (3H, s), 3.20 (2H, s), 2.70 (IH, t), 0.73 (3H, s). LC-MS: rt = 2.29 mm, m/z = 466.2 [M+H]+

Reference： [1]Patent: WO2014/169832,2014,A1 .Location in patent: Page/Page column 178; 179

31
C₂₃H₃₇BrO₃ [ No CAS ]
[ 271-47-6 ]
C₂₉H₄₁N₃O₃ [ No CAS ]
C₂₉H₄₁N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; at 20℃; for 15h;	To a suspension of K2CO3(63 mg, 0.46 mmol) in THF (10 mL) was added lH-pyrazolo [4,3- b]pyridine (55 mg, 0.46 mmol) and compound SJ (100 mg, 0.23 mmol). After stirring at room temperature for 15h, the reaction mixture was poured into 5 mL 0 and extracted with EtOAc (2 x 10 mL). The combined organic layers were washed with brine (2 x 10 mL), dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by reverse-phase prep- HPLC to afford SB-56 as a white solid ( 10.8 mg, 0.023 mmol, 10.0%) and SB-57 as a white solid ( 28.1 mg, 0.059 mmol, 25.5%). SB-56: 1H NMR (400 MHz, CDC13) delta (ppm): 8.80 (IH, s), 8.34 (IH, d), 8.10 (IH, s), 7.64 (IH, dd), 5.27 (IH, AB), 5.25 (IH, AB), 3.53 (2H, q), 3.22 (2H, s), 2.70 (IH, t), 1.21 (3H, t), 0.73 (3H, s). LCMS: Rt = 2.43 mm. m/z = 480.2 [M+H]+. SB-57: 1H NMR (400 MHz, CDCI3) delta (ppm): 9.26 (IH, s), 8.17 (IH, d), 7.98 (IH, s), 7.53 (IH, d), 5.32 (IH, AB), 3.53 (2H, q), 3.22 (2H, s), 2.68 (IH, t), 1.21 (3H, t), 0.72(3H, s). LCMS: Rt = 2.23 mm. m/z = 480.3 [M+H]+.

Reference： [1]Patent: WO2014/169832,2014,A1 .Location in patent: Page/Page column 184; 185

32
[ 1430063-93-6 ]
[ 271-47-6 ]
3α-hydroxy-3β-methyl-21-(pyrazolo[3′,4′-c]pyridin-1′-yl)-19-nor-5β-pregnan-20-one [ No CAS ]
3α-hydroxy-3β-methyl-21-(pyrazolo[3′,4′-c]pyridin-2′-yl)-19-nor-5β-pregnan-20-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10.9%; 10%	With potassium carbonate; In tetrahydrofuran; at 20℃; for 24h;	To a suspension of K2CO3(50 mg, 0.36mmol) in THF (5 niL) was added lH-pyrazolo[3,4- c]pyridine ( 36mg, 0.3mmol) and SA ( 100 mg,0.25 mmol). The mixture was stirred at rt for 24h. The reaction mixture was poured in to 5 mL H20 and extracted with EtOAc (2 x 10 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The residure was purified with by reverse-phase prep-HPLC to afford the title compound as a white solid, SA-20 (lOmg, 9.1% ), SA-21 (12mg, 10.9% ), SA-20:1HNMR (400 MHz, CDCI3), delta (ppm), 9.26 (s, 1H), 8.17 (lH,d), 7.98(s,lH),7.53(lH,d), 5.29(AB,1H),5.20(AB,1H), 2.67(1H, t)0.72 (s, 3H). LC-MS: rt=2.19min,m/z = 436.1 (M++ 1). SA-21:1HNMR (400 MHz, CDC13), delta (ppm), 8.80 (s, 1H), 8.33(lH,d), 8.10(s,lH), 7.65(lH,dd),5.26(AB,1H), 5.24(AB,1H), 2.68(1H, t), 0.72 (s, 3H). LC-MS: rt=2.29 min,m/z = 436.2 (ivT + 1).

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 3500 - 3511
[2]Patent: WO2014/169832,2014,A1 .Location in patent: Page/Page column 107

33
[ 271-47-6 ]
1-cyclopropyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine acetate [ No CAS ]

Reference： [1]Patent: US2014/329820,2014,A1

34
[ 271-47-6 ]
tert-butyl 1-cyclopropyl-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridine-6-carboxylate [ No CAS ]

Reference： [1]Patent: US2014/329820,2014,A1

35
[ 271-47-6 ]
[ 411235-57-9 ]
1-cyclopropyl-1H-pyrazolo[3,4-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With [2,2]bipyridinyl; copper diacetate; sodium carbonate; In 1,2-dichloro-ethane; at 70℃; for 3h;	Copper(II) acetate (3.02 g, 15.1 mmol), 2,2'-bipyridine (2.36 g, 15.1 mmol), and sodium carbonate (3.20 g, 30.2 mmol) were added to a solution of <strong>[271-47-6]1H-pyrazolo[3,4-c]pyridine</strong> (1.80 g, 15.1 mmol) and cyclopropylboronic acid (2.60 g, 30.3 mmol) in 1,2-dichloroethane (50 mL), and the reaction mixture was stirred at 70 C. for 3 hours while open to the atmosphere. The reaction mixture was partitioned between ethyl acetate (300 mL) and saturated aqueous ammonium chloride solution. The resulting aqueous layer was extracted with dichloromethane (2*100 mL), and the combined organic layers were dried, filtered, and concentrated in vacuo. Silica gel chromatography (Gradient: 0% to 30% methanol in ethyl acetate) afforded the product as a yellow oil. Yield: 1.20 g, 7.54 mmol, 50%. 1H NMR (400 MHz, CDCl3) delta 9.17 (dd, J=1, 1 Hz, 1H), 8.34 (d, J=5.7 Hz, 1H), 8.01 (d, J=0.8 Hz, 1H), 7.63 (dd, J=5.7, 1.3 Hz, 1H), 3.70-3.76 (m, 1H), 1.21-1.32 (m, 4H).

Reference： [1]Patent: US2014/329820,2014,A1 .Location in patent: Paragraph 0185

36
C₃₂H₂₅N₅ [ No CAS ]
[ 271-47-6 ]

Yield	Reaction Conditions	Operation in experiment
73 mg	With toluene-4-sulfonic acid; In tetrahydrofuran; water; at 100℃; for 2h;Microwave irradiation; Sealed tube;	General procedure: In a Schlenk tube under nitrogen atmosphere at room temperature were added BINAP (5.5 mol %), Pd(OAc)2 (5 mol %) and Cs2CO3 (1.4 equiv) and toluene (10 mL per mmol of 1bem). The suspension was heated at 80 C for 10 min and benzophenonehydrazone (2.1 equiv) and the chosen substituted starting material 1b-m (1 equiv) were added. The resulting mixture was heated at100 C for the time depicted in Tables 1 and 2. The mixture was poured in water (20 mL per mmol of 1bem) and CH2Cl2 (20 mL per mmol of 1b-m), filtrated on a short pad of Celite, andextracted with CH2Cl2 (320 mL per mmol of 1bem). The combined organic layers were washed with water (320 mL per mmolof 1bem), dried over MgSO4, filtrated and evaporated. The crude product was eluted on a short pad of silica gel using CH2Cl2 aseluent and evaporated. The crude was introduced in a microwavevial with p-toluenesulfonic acid (2 or 3 equiv see Tables 1 and 2) and solvents (see Tables 1 and 2, 10 mL per mmol of 1b-m). The vial was sealed and the suspension was heated at 100 C for the time depicted in Tables 1 and 2. The resulting mixture was poured in water (20 mL per mmol of 1b-m) and extracted with EtOAc (320 mL per mmol of 1bem). The combined layers were driedon MgSO4, filtrated, evaporated purified by silica gel chromatography.

Reference： [1]Tetrahedron,2014,vol. 70,p. 8413 - 8418

37
[ 271-47-6 ]
C₂₃H₃₇BrO₃ [ No CAS ]
C₂₉H₄₁N₃O₃ [ No CAS ]
C₂₉H₄₁N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5%; 8%		To a solution of <strong>[271-47-6]2H-<strong>[271-47-6]pyrazolo[3,4-c]pyridine</strong></strong> (80.8 mg, 0.679 mmol) in THF (3 mL) was added NaH (32.4 mg, 1.35 mmol) at 25C. The mixture was stirred at 20C for 30 mins, then a solution of CI (200 mg, 0.453 mmol) in THF (2 mL) was added. The reaction mixture was stirred at 20C for 16 hrs. The mixture was quenched with water (10 mL), extracted with EtOAc (2 x 15 mL). The combined organic phase was washed with brine (30 mL), dried over Na2S04 and concentrated in vacuum. The residue was purified by preparative TLC (eluted with EtOAc) to give compound 46 (9.9 mg, 5%) and compound 47 (17.3 mg, 8%). [402] 46: 1H NMR (400 MHz, CDC13) delta 9.31 (s, 1H), 8.19 (d, J = 6.0 Hz, 1H), 8.00 (s, 1H), 7.62-7.52 (m, 1H), 5.38-5.18 (m, 2H), 3.54 (d, = 9.0 Hz, 1H), 3.33 (s, 3H), 3.21 (d, = 9.0 Hz, 1H), 2.71-2.61 (m, 1H), 2.29-2.10 (m, 2H), 1.98-1.60 (m, 9H), 1.50-1.27 (m, 11H), 1.22-1.09 (m, 2H), 0.91-0.76 (m, 2H), 0.70 (s, 3H). LCMS Rt = 1.039 min in 2 min chromatography, MS ESI calcd. for C29H42N303 [M+H]+ 480, found 480. [403] 47: 1H NMR (400 MHz, CDC13) delta 8.79 (s, 1H), 8.34 (d, = 5.5 Hz, 1H), 8.10 (s, 1H), 7.64 (dd, = 1.1, 5.6 Hz, 1H), 5.31-5.19 (m, 2H), 3.54 (d, = 9.0 Hz, 1H), 3.34 (s, 3H), 3.22 (d, = 9.0 Hz, 1H), 2.71-2.63 (m, 1H), 2.27-2.09 (m, 2H), 1.98-1.87 (m, 2H), 1.83-1.61 (m, 6H), 1.56-1.40 (m, 8H), 1.37-1.27 (m, 6H), 1.22-1.10 (m, 2H), 0.71 (s, 3H). LCMS Rt = 1.069 min in 2 min chromatography, MS ESI calcd. for C29H42N303 [M+H]+ 480, found 480.

Reference： [1]Patent: WO2016/134301,2016,A2 .Location in patent: Paragraph 401-403

38
[ 1011464-52-0 ]
[ 271-47-6 ]
ethyl 4-(isopropylamino)-6-(1H-pyrazolo[3,4-c]pyridin-1-yl)nicotinate [ No CAS ]
C₁₇H₁₉N₅O₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 7420 - 7427

39
[ 3934-20-1 ]
[ 271-47-6 ]
2-chloro-4-(pyrazolo[3.4-c]pyrid-1-yl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of pyrazolo[3.4-c]pyridine (2.56 g, 21.5 mmol) in DMF (60 mL) is added NaH (60% in mineral oil,1.03 g, 25.78 mmol) portionwise at 0 C. After stirring at 0 C for 30 min.2,4-dichloropyrimidine (3.20 g, 21.5 mmol) is added, and the mixture is allowed to stir at 15 C for 12 hrs. The resulting mixture is quenched with water (200 mL) and the mixture is extracted with EtOAc (100 mL x 3), and washed with water (100 mL x 4), dried with Na2SO4 and concentrated in vacuo. The residue is purified by silica gel chromatography (petroleum ether: EtOAc =10:1), to give 2-chloro-4-(pyrazolo[3.4-c]pyrid-1-ylpyrimidine.

Reference： [1]Patent: WO2017/120429,2017,A1 .Location in patent: Page/Page column 314

40
[ 271-47-6 ]
2-chloro-N-(2,4-dimethoxybenzyl)-5-nitrobenzenesulfonamide [ No CAS ]
N-(2,4-dimethoxybenzyl)-5-nitro-2-(2H-pyrazolo[3,4-c]pyridin-2-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate; In acetonitrile; at 120℃; for 2h;Microwave irradiation;	To a solution of 2-chloro-N-(2 ,4-d imethoxybenzyl)-5-n itrobenzenesulfonamide (700 mg,1.81 mmol) in acetonitrile (18 mL) were added 1H-<strong>[271-47-6]pyrazolo[3,4-c]pyridine</strong> (307 mg,2.58 mmol, CAS-RN 271-47-6) and powdered potassium carbonate (750 mg, 5.43 mmol)and the mixture was irradiated for 2h at 12000 in the microwave. The reaction mixture wasfiltered and concentrated in vacuo, and the residue was extracted with dichloromethaneand water. The aqueous phase was washed three times with dichloromethane. Then thecombined organic phases were washed with brine and dried using a Whatman filter. Concentration under reduced pressure led to the title compound that was purified by flash chromatography (610 mg, 72% yield, 95% purity).LC-MS (Method B): Rt = 1.15 mm, MS (ESIpos): mlz = 470 [M+H]1HNMR (400MHz, DMSO-d6) oe [ppm]: 3.55 (s, 3H), 3.64 (s, 3H), 4.15 (d, 2H), 6.19 (d,1H), 6.29 (dd, 1H), 7.07 (d, 1H), 7.96 (dd, 1H), 7.99 (t, 1H), 8.10 (d, 1H), 8.33 (d, 1H),8.45 (d, 1H), 8.50 (dd, 1H), 8.71 (d, 1H), 9.00 (s, 1H).

Reference： [1]Patent: WO2017/191000,2017,A1 .Location in patent: Page/Page column 129

41
[ 271-47-6 ]
C₂₂H₃₅BrO₃ [ No CAS ]
C₂₈H₃₉N₃O₃ [ No CAS ]
C₂₇H₃₇N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8 mg; 6 mg	With potassium carbonate; In acetone; at 15℃; for 16h;Inert atmosphere;	To a suspension of 2H-pyrazolo[3,4-c]py (125 mg, 1.05 mmol) and K2CO3 (193 mg, 1.40 mmol) in acetone (10 mL) was added Jl (300 mg, 0.701 mmol) at 15C under N2. The mixture was stirred at 15C for 16 hrs. The mixture was filtered and concentrated to give a solid, which was purified by pre-HPLC (Column:Xtimate C18 15025mm5um; Condition: water(0.05%HCl)-ACN; Gradient 16%-41%B; Gradient Time(min):9.5) to afford Compound 27 (8.00 mg, 2% ) as a solid and Compound 28 (6.00 mg, 2%) as a solid. (0620) Compound 27: 1H NMR (400 MHz, CDC13) delta 9.25 (s, 1H), 8.19-8.14 (m, 1H), 7.98 (s, 1H), 7.55-7.50 (m, 1H), 5.36-5.20 (m, 2H), 3.87-3.85 (m, 1H), 2.75-2.70 (m, 1H), 2.33-1.72 (m, 5H), 1.50-1.12 (m, 19H), 0.90-0.77 (m, 4H), 0.71 (s, 3H). LCMS Rt = 0.725 min in 1.5 min chromatography, 5-95 AB, purity 100 %, MS ESI calcd. for C28H40N3O3 [M+H]+ 466, found 466. (0621) Compound 28: (0622) 1H NMR (400 MHz, CDC13) delta 8.80 (s, 1H), 8.36-8.32 (m, 1H), 8.09 (s, 1H), 7.65-7.60 (m, 1H), 5.32-5.20 (m, 2H), 3.87-3.85 (m, 1H), 2.75-2.68 (m, 1H), 2.33-1.68 (m, 7H), 1.50-1.18 (m, 18H), 0.77 (s, 3H), 0.72 (s, 3H). (0623) LCMS Rt = 0.748 min in 1.5 min chromatography, 5-95 AB, purity 100 %, MS ESI calcd. for C28H40N3O3 [M+H]+ 466, found 466.

Reference： [1]Patent: WO2018/13615,2018,A1 .Location in patent: Page/Page column 136-137

42
[ 271-47-6 ]
C₂₃H₃₇BrO₃ [ No CAS ]
C₂₉H₄₁N₃O₃ [ No CAS ]
C₂₉H₄₁N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8 mg; 12%	With potassium carbonate; In acetone; at 15℃; for 16h;	To a solution of XI (150 mg, 0.339 mmol) in acetone (2 mL) was added 2H-pyrazolo [3,4- c]pyridine (60.5 mg, 0.508 mmol) and K2C03 (92.8 mg, 0.678 mmol). After stirring at 15C for 16 hrs, the reaction mixture was treated with water (5 mL) and extracted with EtOAc (2 x 10 mL). The combined organic layer was washed with brine (5 mL). The organic layer was dried over Na2SC>4, filtered and concentrated. The residue was purified by HPLC (column: Waters Xbridge 150*25 5u), water (lOmM NH4HC03)-ACN, gradient: 45-65% B, flow rate: 25 mL/min)) to give Compound 55 (20 mg, 12%) as a solid and Compound 54 (15 mg, impure) as a solid, which was combined with another batch prepared from 50 mg of XI. The impure sample was further purified by prep-TLC (PE/EtOAc = 1/1) to give Compuond 54 (8 mg) as a solid. (0813) Compound 54: (0814) 1H NMR (400 MHz, CDC13) delta 9.40-9.20 (m, 1H), 8.25-8.10 (m, 1H), 8.10-8.00 (m, 1H), 7.70- 7.55 (m, 1H), 5.39-5.12 (m, 2H), 3.63-3.10 (m, 1H), 3.52-3.48 (m, 1H), 3.42 (s, 3H), 2.34-2.01 (m, 3H), 2.00-1.62 (m, 10H), 1.62-1.48 (m, 5H), 1.48-0.97 (m, 6H), 0.82 -0.63 (m, 6H). (0815) LCMS Rt = 0.766 min in 2 min chromatography, 30-90AB_2MIN_E, purity 100%, MS ESI calcd. for C29H42N3O3 [M+H]+ 480 found 480. (0816) Compound 55: (0817) 1H NMR (400 MHz, CDCI3) delta 8.81-8.78 (m, 1H), 8.36-8.32 (m, 1H), 8.08 (s, 1H), 7.65-7.61 (m, 1H), 5.28-5.12 (m, 2H), 3.70-3.60 (m, 1H), 3.52-3.48 (m, 1H), 3.41 (s, 3H), 2.21-2.01 (m, 2H), 1.84-1.65 (m, 4H), 1.65-1.48 (m, 6H), 1.48-1.19 (m, 10H), 1.19-0.98 (m, 2H), 0.82 -0.70 (m, 6H). (0818) LCMS Rt = 0.793 min in 2 min chromatography, 30-90AB_2MIN_E, purity 100%, MS ESI calcd. for C29H42N3O3 [M+H]+ 480 found 480.

Reference： [1]Patent: WO2018/13615,2018,A1 .Location in patent: Page/Page column 169-170

43
C₂₃H₃₇BrO₃ [ No CAS ]
[ 271-47-6 ]
C₂₉H₄₁N₃O₃ [ No CAS ]
C₂₉H₄₁N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5 mg; 10 mg	With potassium carbonate; In acetone; at 25℃; for 16h;	Compound 63 To a mixture of Tl (500 mg, 1.13 mmol) and K2CO3 (312 mg, 2.26 mmol) in acetone (5 mL) was added lH-pyrazolo[3,4-b]pyridine (201 mg, 1.69 mmol) at 25C. The reaction mixture was stirred at the 25C for 16 h. The reaction mixture was filtered and the filtrate was concentrated in vacuum to give crude product which was purified by prep. HPLC (column: Agela Durashell C18 150* 25 5u, gradient: 30-60% B (A= 0.05% HC1- ACN, B= acetonitrile), flow rate: 30 mL/min) to give Compound 62 (30 mg, impure) as a solid and Compound 63 (10 mg, 2%) as a solid. The impure Compound 62 (30 mg, impure) was purified by SFC separation (Column: AS (250 mm * 30 mm, 5 urn), Mobile phase: Supercritical C02 /MeOH+ NH3H20 = 25/25, Flow rate: 50 ml/min, Wavelength: 220 nm) to give Compound 62 (5 mg, 1%) as a solid. Compound 62: (0863) 1H NMR (400MHz, CDC13) delta 9.28-9.26 (m, IH), 8.20-8.14 (m, IH), 7.95 (s, IH), 7.64-7.43 (m, IH), 5.74 (d, J= 17.4 Hz, IH), 5.29 (d, J= 17.4 Hz, IH), 3.46 (s, 3H), 3.25-3.20 (m, IH), 2.82-2.73 (m, IH), 2.22-2.06 (m, 2H), 1.80-1.67 (m, 4H), 1.43-1.33 (m, 4H), 1.30-1.11 (m, 1 IH), 1.00-0.82 (m, 3H), 0.78 (s, 3H), 0.71 (s, 3H) (0864) LCMS Rt = 0.794 min in 2 min chromatography, 30-90 AB, purity 100%, MS ESI calcd. For C29H42N3O3 [M+H]+ 480, found 480. (0865) Compound 63: (0866) 1H NMR (400MHz, CDC13) delta 9.52-9.30 (m, IH), 8.45-8.32 (m, IH), 8.20-8.12 (m, IH), 6.13- 6.09 (m, IH), 5.80-5.60 (m, IH), 3.50 (s, 3H), 3.35-3.30 (m, IH), 2.96-2.92 (m, IH), 2.15-2.08 (m, 2H), 1.90-1.67 (m, 4H), 1.43-1.33 (m, 6H), 1.30-1.11 (m, 10H), 1.00-0.82 (m, 3H), 0.78 (s, 3H), 0.71 (s, 3H) (0867) LCMS Rt = 0.816 min in 2 min chromatography, 30-90 AB, purity 100%, MS ESI calcd. For C29H42N3O3 [M+H]+ 480, found 480.

Reference： [1]Patent: WO2018/13615,2018,A1 .Location in patent: Page/Page column 179-180

44
C₂₂H₃₅BrO₃ [ No CAS ]
[ 271-47-6 ]
C₂₈H₃₉N₃O₃ [ No CAS ]
C₂₈H₃₉N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20 mg; 50 mg	With potassium carbonate; In acetone; at 25℃; for 16h;	To a mixture of VI (400 mg, 0.936 mmol) and K2CO3 (258 mg, 1.87 mmol) in acetone (5 mL) was added lH-pyrazole-4-carbonitrile (166 mg, 1.40 mmol) at 25C. The reaction mixture was stirred at the 25C for 16 h. The reaction mixture was quenched with water (20 mL) and extracted with EtOAc (2 x 20 mL). The combined organic layer was dried over Na2SC>4, filtered and concentrated in vacuum to give crude product, which was purified by prep. (0767) HPLC (column: Boston Green ODS 150 * 30 5u, gradient: 34-44% B (A= 0.1% TFA-ACN, B= acetonitrile), flow rate: 30 mL/min) to give mixture of Compound 49 and Compound 50 (120 mg, crude) as yellow oil. The oil was purified by SFC (column: OD (250 mm * 30 mm, 5 um); Mobile phase: Supercritical C02 /MeOH + NH3H2O = 40/40; Flow rate: 50 ml/min; (0768) Wavelength: 220 nm) to give Compound 49 (20 mg, 17%) as a solid and Compound 50 (50 mg, 42%) as a solid. (0769) Compound 49: (0770) 1H NMR (400MHz, CDCI3) delta 9.28 (s, 1H), 8.17 (d, J= 5.6 Hz, 1H), 7.99 (s, 1H), 7.52 (d, J = 5.6 Hz, 1H), 5.81 (d, J= 17.6 Hz, 1H), 5.37 (d, J= 17.6 Hz, 1H), 3.61-3.56 (m, 1H), 2.66-2.60 (m, 2H), 2.21-2.08 (m, 1H), 1.92-1.64 (m, 4H), 1.54-1.44 (m, 4H), 1.42-1.31 (m, 4H), 1.30- 1.25 (m, 3H), 1.21 (s, 3H), 1.18-1.05 (m, 3H), 0.97-0.85 (m, 2H), 0.77 (s, 3H), 0.73 (s, 3H). (0771) LCMS Rt = 0.655 min in 2 min chromatography, 30-90 AB, purity 100%, MS ESI calcd. For C28H40N3O3 [M+H]+ 466, found 466. Compound 50: (0772) 1H NMR (400MHz, CDCI3) delta 8.92 (s, 1H), 8.33-8.31 (m, 1H), 8.11 (s, 1H), 7.65-7.63 (m, 1H), 5.91 (d, J = 18.4 Hz, 1H), 5.35 (d, J= 18.4 Hz, 1H), 3.65-3.61 (m, 1H), 2.73-2.67 (m, 1H), 2.62-2.60 (m, 1H), 2.19-2.07 (m, 1H), 1.90-1.64 (m, 4H), 1.54-1.44 (m, 4H), 1.43-1.32 (m, 4H), 1.31-1.22 (m, 4H), 1.21 (s, 3H), 1.19-1.07 (m, 2H), 0.97-0.86 (m, 2H), 0.77 (s, 3H), 0.73 (s, 3H). (0773) LCMS Rt = 0.690 min in 2 min chromatography, 30-90 AB, purity 100%, MS ESI calcd. For C28H40N3O3 [M+H]+ 466, found 466.

Reference： [1]Patent: WO2018/13615,2018,A1 .Location in patent: Page/Page column 161-162

45
C₂₃H₃₇BrO₂ [ No CAS ]
[ 271-47-6 ]
C₂₉H₄₁N₃O₂ [ No CAS ]
C₂₉H₄₁N₃O₂ [ No CAS ]
C₂₉H₄₁N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3 mg; 17 mg; 15 mg	With potassium carbonate; In acetone; at 25℃; for 10h;	To a solution of AB1 (150 mg, 0.352 mmol) and lH-pyrazolo[3,4-c]pyridine (43.9 mg, 0.369 mmol) in acetone (3 mL) was added K2CO3 (97.2 g, 0.704 mmol) at 25C. After stirring at 25C for 10 hrs, the mixture was poured into water (50 mL) and extracted with EtOAc (3 x 20 mL). The combined organic layer was washed with brine (50 mL), dried over Na2S04i filtered and concentrated to afford crude product (100 mg), which was purified by preparative HPLC (column: YMC-Actus Triart C18 15030mm5um)), gradient: 40-70% B (A = 0.1%HC1, B = ACN), flow rate: 25 mL/min) to afford Compound 85 (15 mg, 9%) as a solid, Compound 84 (17 mg, 10%) as a solid and Compound 83 (20 mg, impure). Compound 83 (20 mg, impure) was purified by SFC separation (column: AD (250mm*30mm, lOum)), gradient: 50-50% B (A = 0.1%NH3H2O, B = EtOH), flow rate: 80 mL/min) to afford Compound 83 (3 mg, yield 15%) as a solid. (0970) Compound 83: 1H NMR (400MHz, CDC13) delta 9.26 (s, 1H), 8.17 (d, J= 4.8 Hz, 1H), 7.98 (s, 1H), 7.53 (d, J = 6.0 Hz, 1H), 5.34-5.16 (m, 2H), 2.78-2.70 (m, 1H), 2.27 (d, J= 8.4 Hz, 1H), 2.07-2.01 (m, 1H), 1.73-1.59 (m, 3H), 1.54-1.45 (m, 5H), 1.42-1.24 (m, 11H), 1.21 (s, 3H), 0.98 (d, J = 6.8 Hz, 3H), 0.86-0.80 (m, 1H), 0.76 (s, 3H), 0.73 (s, 3H). LCMS Rt = 2.405 min in 4 min chromatography, 10-80AB, purity 99%, MS ESI calcd. For C29H42N3O2 [M +H]+ 464, found 464. (0971) Compound 84: (0972) 1H NMR (400MHz, CDC13) delta 8.78 (s, 1H), 8.34 (d, J= 5.6 Hz, 1H), 8.10 (s, 1H), 7.65-7.63 (m, 1H), 5.28-5.17 (m, 2H), 2.76-2.65 (m, 1H), 2.29-2.26 (m, 1H), 2.10-2.02 (m, 1H), 1.72- 1.60 (m, 3H), 1.55-1.48 (m, 5H), 1.42-1.34 (m, 4H), 1.32-1.19 (m, 10H), 0.96 (d, J= 7.2 Hz, 3H), 0.88-0.82 (m, 1H), 0.77 (s, 3H), 0.74 (s, 3H). (0973) LCMS Rt = 2.014 min in 3 min chromatography, 10-80AB, purity 100%, MS ESI calcd. For C29H42N3O2 [M +H]+ 464, found 464. Compound 85: (0974) 1H NMR (400MHz, CDC13) delta 9.03 (s, 1H), 8.56 (s, 1H), 7.87 (d, J= 6.8 Hz, 1H), 7.18 (d, J = 8.0 Hz, 1H), 5.32-5.18 (m, 2H), 3.80-2.74 (m, 1H), 2.35-2.32 (m, 1H), 2.01-1.98 (m, 1H), 1.71- 1.51 (m, 6H), 1.45-1.24 (m, 13H), 1.22 (s, 3H), 1.03 (d, J= 7.2 Hz, 3H), 0.91-0.86 (m, 1H), 0.77 (s, 3H), 0.74 (s, 3H). LCMS Rt = 2.388 min in 4 min chromatography, 10-80AB, purity 98.7%, MS ESI calcd. For C29H42N3O2 [M +H]+ 464, found 464.

Reference： [1]Patent: WO2018/13615,2018,A1 .Location in patent: Page/Page column 197-199

46
C₂₄H₃₉BrO₂ [ No CAS ]
[ 271-47-6 ]
C₃₀H₄₃N₃O₂ [ No CAS ]
C₃₀H₄₃N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11 mg; 36 mg	With potassium carbonate; In acetone; at 25℃; for 12h;	To a mixture of AC1 (150 mg, 0.341 mmol) and K2C03 (94.2 mg, 0.682 mmol) in acetone (3 mL) was added lH-pyrazolo[3,4-c]pyridine (42.6 mg, 0.358 mmol) at 25C. After stirring at 25C for 12 hrs, the mixture was poured into water (50 mL) and extracted with EtOAc (3 x 20 mL). The combined organic layer was washed with brine (50 mL), dried over with Na2SC>4, filtered and concentrated to afford crude product, which was purified by prep-HPLC separation (column: YMC-Actus Triart C18 15030mm5um)), gradient: 45-75% B (A = 0.1%HC1, B = ACN), flow rate: 25 mL/min) to afford Compound 87 (36 mg, 22%) as a solid and Compound 86 (20 mg, impure). The crude Compound 86 was purified by SFC separation (column: (0981) AD(250mm*30mm,10um)), gradient: 45-45% B (A = 0.1%NH3H20 , B = ETOH), flow rate: 80 mL/min) to afford Compound 86 (11 mg, 7%) as a solid. (0982) Compound 86: (0983) 1H NMR (400MHz, CDC13) delta 9.28 (s, 1H), 8.25-8.1 (m, 1H), 8.02 (s, 1H), 7.65-7.55 (m, 1H), 5.37-5.19 (m, 2H), 2.58-2.5 (m, 1H), 2.33 (d, J= 12 Hz, 1H), 2.10-2.05 (m, 1H), 1.72-1.65 (m, 2H), 1.53-1.45 (m, 5H), 1.42-1.23 (m, 12H), 1.21 (s, 3H), 1.16 (s, 1H), 1.01-0.93 (m, 1H), 0.83 (t, J= 8.0 Hz, 4H), 0.77 (s, 3H), 0.73 (s, 3H). (0984) LCMS Rt = 2.502 min in 4.0 min chromatography, 10-80AB.lcm, purity 100%, MS ESI calcd. for C30H44N3O2 [M+H]+ 478, found 478. (0985) Compound 87: 1H NMR (400MHz, CDC13) delta 9.26 (s, 1H), 8.17 (d, J= 4.0 Hz, 1H), 7.97 (s, 1H), 7.54-7.50 (m, 1H), 5.35-5.17 (m, 2H), 2.60-2.52 (m, 1H), 2.35-2.30 (m, 1H), 2.10-2.04 (m, 1H), 1.69- 1.62 (m, 4H), 1.52-1.46 (m, 5H), 1.39-1.26 (m, 11H), 1.21 (s, 3H), 1.12-0.98 (m, 1H), 0.83 (t, J = 8.0 Hz, 4H), 0.76 (s, 3H), 0.73 (s, 3H) LCMS Rt = 1.750 min in 3.0 min chromatography, 10-80AB_3MIN_E.M, purity 100%, MS ESI calcd. for C30H44N3O2 [M+H]+ 478, found 478.

Reference： [1]Patent: WO2018/13615,2018,A1 .Location in patent: Page/Page column 199-201

47
C₂₅H₄₁BrO₂ [ No CAS ]
[ 271-47-6 ]
C₃₁H₄₅N₃O₂ [ No CAS ]
C₃₁H₄₅N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%; 19%	With potassium carbonate; In acetone; at 15℃; for 20h;	To a solution of AE1 (150 mg, 0.33 mmol) in acetone (5 mL) was added K2CO3 (91 mg, 0.66 mmol) and lH-pyrazolo[3,4-c]pyridine (39.3 mg, 0.33 mmol). The mixture was stirred at 15C for 12 hrs. Second batch of K2CO3 (45.5 mg, 0.33 mmol) and lH-pyrazolo[3,4- cjpyridine (7.86 mg, 0.06 mmol) was added at 15C. The mixture was stirred at 15C for another 8 hrs and poured in to water (10 mL), extracted with ethyl acetate (3 x 10 mL). The combined organic layer was washed with brine (20 mL), dried over Na2SC>4, filtered and concentrated in vacuum. The residue was purified by flash column (0-80% of EtOAc in PE) to afford Compound 78 (70 mg, impure) as a solid and Compound 79 (31 mg, 19%) as a solid. The impure Compound 78 (70 mg, 0.14 mmol) was purified by SFC (column: AS(250mm30mm,5um)), gradient: 35-35% B (A= 0.1%NH3/H2O, B= EtOH ), flow rate: 50 mL/min) to give a solid, which was further purified by re-crystallized from MeCN (3 mL) to give Compound 78 (36 mg, 22%) as a solid. (0946) Compound 78: H NMR (400 MHz, CDC13) delta 8.77 (s, 1H), 8.38-8.29 (m, 1H), 8.09 (s, 1H), 7.66-7.61 (m, 1H), 5.33-5.21 (m, 2H), 2.53-2.42 (m, 2H), 2.13-2.04 (m, 1H), 1.75-1.65 (m, 2H), 1.56-1.23 (m, 15H), 1.21 (s, 3H), 1.21-1.14 (m, 2H), 1.03-0.91 (m, 1H), 0.88-0.79 (m, 7H), 0.76 (s, 3H), 0.71 (s, 3H). (0947) LCMS Rt = 0.968 min in 2 min chromatography, 30-90AB_2MIN_E, purity 100%, MS ESI calcd. for C31H46N3O2 [M+H]+ 492, found 492. (0948) Compound 79: (0949) 1H NMR (400 MHz, CDC13) delta 9.26 (s, 1H), 8.18-8.14 (d, J= 6 Hz, 1H), 7.96 (s, 1H), 7.54-7.49 (m, 1H), 5.37-5.18 (m, 2H), 2.53-2.44 (m, 2H), 2.12-2.03 (m, 1H), 1.74-1.66 (m, 2H), 1.52- 1.28 (m, 12H), 1.26-1.13 (m, 8H), 1.03-0.92 (m, 1H), 0.87-0.82 (m, 4H), 0.81-0.75 (m, 6H), 0.71 (s, 3H). (0950) LCMS Rt = 0.917 min in 2 min chromatography, 30-90AB, purity 100%, MS ESI calcd. for C31H46N3O2 [M+H]+ 492, found 492.

Reference： [1]Patent: WO2018/13615,2018,A1 .Location in patent: Page/Page column 194-195

48
C₂₃H₃₇BrO₂ [ No CAS ]
[ 271-47-6 ]
C₂₉H₄₁N₃O₂ [ No CAS ]
C₂₉H₄₁N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48 mg; 18 mg		To a solution of lH-pyrazolo[3,4-c]pyridine (139 mg, 1.17 mmol) in THF (10 mL) was added NaH (89.5 g, 2.24 mmol, 60%) in portions at 25C. The mixture was stirred at 60C for 10 min. Then D6 (480 mg, 1.12 mmol) in THF (10 mL) was added drop-wise to the solution. The mixture was stirred at 60C for 1 h. The mixture was poured into water (50 mL) and extrated with EtOAc (3 x 20 mL). The combined organe layer was washed with brine (50 mL), dried over with Na2S04 and concentrated to afford crude product. The residue was purified by silica gel chromatography (100-200 mesh silica gel, Petroleum ether/Ethyl acetate=0/l) to afford the mixture of D7 and D8 (290 mg, crude) as a solid. D8 (290 mg, 0.62 mmol) was purified by SFC (column: OD(250mm*30mm,10um)), gradient: 40-40% B (A= 0.1%NH3/H2O, B= EtOH ), flow rate: 80 mL/min) to give pure Compound 9 (48 mg, 16%) and pure Compound 10 (18 mg, 6%) as a solid. (0506) Compound 9: (0507) 1H NMR (400 MHz, CDC13) delta 8.8 (s, 1H), 8.39-8.29 (m, 1H), 8.1 (s, 1H), 7.68-7.61 (d, J = 4.8 Hz, 1H), 5.32-5.19 (m, 2H), 2.76-2.62 (m, 1H), 2.27-2.06 (m, 2H), 1.84-1.67 (m, 4H), 1.53- 1.26 (m, 11H), 1.23-1.09 (m, 7H), 1.08-1.01 (m, 1H), 0.96-0.89 (d, J = 7.2 Hz, 3H), 0.77 (s, 3H), 0.71 (s, 3H). (0508) LCMS Rt = 0.885 min in 2 min chromatography, 30-90AB_2MIN_E, purity 100%, MS ESI calcd. for C29H42N3O2 [M+H]+ 464, found 464. (0509) SFC Rt = 1.785 min in 3 min chromatography, OD-H_3UM_3_5_40_4ML_3MIN, purity: 100%. (0510) Compound 10: (0511) 1H NMR (400 MHz, CDC13) delta 8.80 (s, 1H), 8.39-8.28 (m, 1H), 8.09 (s, 1H), 7.69-7.61 (d, J = 4.8 Hz, 1H), 5.34-5.17 (m, 2H), 2.68-2.57 (m, 1H), 2.24-2.09 (m, 2H), 1.96-1.71 (m, 4H), 1.47- 1.13 (m, 15H), 1.07-0.81 (m, 7H), 0.73 (s, 6H). LCMS Rt = 0.908 min in 2 min chromatography, 30-90AB_2MIN_E, purity 98%, MS ESI calcd. for C29H42N3O2 [M+H]+ 464, found 464. (0512) SFC Rt = 2.132 min in 3 min chromatography, OD-H_3UM_3_5_40_4ML_3MIN, purity: 99%.

Reference： [1]Patent: WO2018/13615,2018,A1 .Location in patent: Page/Page column 113-114

49
C₂₃H₃₇BrO₂ [ No CAS ]
[ 271-47-6 ]
C₂₉H₄₁N₃O₂ [ No CAS ]
C₂₉H₄₁N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5 mg; 15 mg	With potassium carbonate; In acetone; at 25℃; for 12h;	To a mixture of D6 (500 mg, 1.17 mmol) and K2CO3 (323 mg, 2.34 mmol) in acetone (3 mL) was added lH-pyrazolo[3,4-c]pyridine (1.45 mg, 1.22 mmol) at 25C. The mixture was stirred at 25C for 12 h. The mixture was poured into water (50 mL) and extracted with EtOAc (3 x 20 mL). The combined organic layer was washed with brine (50 mL), dried over with Na2SC>4, filtered and concentrated to afford crude product, which was purified by prep-HPLC separation (column: Phenomenex Synergi C18 15030mm4um)), gradient: 28-58% B (A = 0.1%HC1, B = ACN), flow rate: 30 mL/min) and then SFC (column: OJ(250mm*30mm,10um)), gradient: 35-35% B (A = 0.1%NH3H2O , B = ETOH), flow rate: 80 mL/min) to afford Compound 8 (15 mg, yield 75%) as a solid and Compound 7 (5 mg, yield 25%) as a solid. (0515) Compound 7: (0516) 1H NMR (400MHz, CDC13) delta 9.26 (s, 1H), 8.27-8.17 (m, 1H), 7.98 (s, 1H), 7.58-7.49 (m, 1H), 5.32 (d, J = 16.0 Hz, 1H), 5.22 (d, J = 16.0 Hz, 1H), 2.62 (t, J= 8.0 Hz, 1H), 2.24-2.09 (m, 2H), 1.97-1.89 (m, 1H), 1.81-1.72 (m, 2H), 1.52-1.42 (m, 4H), 1.37-1.13 (m, 14H), 1.05-0.98 (m, 1H), 0.96 (d, J= 8.0 Hz, 3H), 0.90-0.82 (m, 1H), 0.74-0.71 (m, 6H). (0517) LCMS Rt = 2.406 in in 4.0 min chromatography, 10-80AB.lcm, purity 99.3%, MS ESI calcd. for C29H42N3O2 [M+H]+ 464, found 464. (0518) Compound 8: 1H NMR (400MHz, CDC13) delta 9.26 (s, 1H), 8.17 (d, J= 8.0 Hz, 1H), 7.98 (s, 1H), 7.52 (dd, J=1.0, 8.0 Hz, 1H), 5.32 (d, J= 16.0 Hz, 1H), 5.22 (d, J = 16.0 Hz, 1H), 2.67 (t, J= 8.0 Hz, 1H), 2.28-2.18 (m, 1H), 2.11-2.08 (m, 1H), 1.85-1.67 (m, 5H), 1.65-1.36 (m, 10H), 1.27-1.12 (m, 7H), 1.04 (br d, J=13.3 Hz, 1H), 0.93 (d, J= 8.0 Hz, 3H), 0.77 (s, 3H), 0.71 (s, 3H). LCMS Rt = 2.358 in in 4.0 min chromatography, 10-80AB.lcm, purity 99.7%, MS ESI calcd. for C29H42N3O2 [M+H]+ 464, found 464.

Reference： [1]Patent: WO2018/13615,2018,A1 .Location in patent: Page/Page column 115-116

50
C₂₄H₃₉BrO₃ [ No CAS ]
[ 271-47-6 ]
C₃₀H₄₃N₃O₃ [ No CAS ]
C₃₀H₄₃N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9 mg	With potassium carbonate; In acetone; at 25℃; for 10h;	Example 11. Syntheses of Compounds 21 and 22. (0586) (0587) Compound 22 (0588) To a solution of the Gl (150 mg, 0.329 mmol) and lH-pyrazolo[3,4-c]pyridine (41 mg, 0.345 mmol) in acetone (3 mL) was added K2CO3 (26.1 g, 0.658 mmol) at 25C. After stirring at 25C for 10 hrs, the mixture was poured into water (50 mL) and extracted with EtOAc (3 x 20 mL). The combined organic layer was washed with brine (50 mL), dried over with Na2S04i filtered and concentrated to afford crude product, which was purified by prep. HPLC (column: YMC-Actus Triart C18 15030mm5um)), gradient: 30-60% B (A = 0.1%HC1, B = ACN), flow rate: 25 mL/min) to afford Compound 22 (3 mg, impure) as a solid and Compound 21 (20 mg, impure). Compound 21 (20 mg, impure) was purified by flash column (0-30% of EtOAc in PE) to give Compound 21 (9 mg, 6%) as a solid. (0589) 1H NMR (400MHz, CDC13) delta 9.26 (s, 1H), 8.17 (d, J= 4.8 Hz, 1H), 7.98 (s, 1H), 7.53 (d, J = 6.8 Hz, 1H), 5.36-5.20 (m, 2H), 3.38-3.36 (m, 1H), 3.32-3.31 (m, 1H), 3.27 (s, 3H), 2.70-2.61 (m, 1H), 2.30-2.19 (m, 1H), 2.17-2.13 (m, 1H), 2.04-1.95 (m, 1H), 1.85-1.74 (m, 2H), 1.56- 1.49 (m, 6H), 1.45-1.22 (m, 12H), 1.17-1.14 (m, 1H), 0.93-0.88 (m, 1H), 0.73 (s, 6H). (0590) LCMS Rt = 1.771 min in 3.0 min chromatography, 10-80AB, purity 100%, MS ESI calcd. For C30H44N3O3 [M+H]+ 494, found 494.

Reference： [1]Patent: WO2018/13615,2018,A1 .Location in patent: Page/Page column 128-129

51
C₂₄H₃₉BrO₃ [ No CAS ]
[ 271-47-6 ]
C₃₀H₄₃N₃O₃ [ No CAS ]
C₃₀H₄₃N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50 mg; 8 mg	With potassium carbonate; In acetone; at 25℃; for 12h;	To a mixture of HI (150 mg, 0.329 mmol) and K2CO3 (90.9 mg, 0.658 mmol) in acetone (3 mL) was added lH-pyrazolo[3,4-c]pyridine (41 mg, 0.345 mmol) at 25C. After stirring at 25C for 12 h, the mixture was poured into water (50 mL) and extracted with EtOAc (3 x 20 mL). The combined organic layer was washed with brine (50 mL), dried over with Na2SC>4, filtered and concentrated to afford crude product, which was purified by preparative HPLC (column: YMC-Actus Triart CI 8 150 * 30 mm * 5 urn)), gradient: 35-65% B (A = 0.1% HC1, B = ACN), flow rate: 25 mL/min) to afford Compound 23 (50 mg, 31%) as a solid and (0593) Compound 24 (20 mg, impure). Compound 24 (20 mg, impure) was purified by SFC separation (column: AD (250 mm * 30 mm, 10 urn)), gradient: 45-45% B (A = 0.1% NH3H20, B = EtOH), flow rate: 80 mL/min) to afford Compound 24 (8 mg, 5%) as a solid. (0594) Compound 23: *H NMR (400MHz, CDC13) delta 8.79 (s, 1H), 8.34 (d, J= 5.6 Hz, 1H), 8.09 (s, 1H), 7.66-7.63 (m, 1H), 5.23-5.30 (m, 2H), 3.56-3.48 (m, 1H), 3.42-3.37 (m, 1H), 3.33 (s, 3H), 2.69-2.66 (m, 1H), 2.27-2.17 (m, 1H), 2.14-2.07 (m, 1H), 1.97-1.84 (m, 2H), 1.80-1.65 (m, 4H), 1.55-1.28 (m, 13H), 1.21 (s, 3H), 1.10-1.04 (m, 1H), 0.80 (s, 3H), 0.71 (s, 3H). (0595) LCMS Rt = 2.290 min in 4.0 min chromatography, 10-80AB, purity 99.1%, MS ESI calcd. For C30H44N3O3 [M+H]+ 494, found 494. Compound 24: (0596) 1H NMR (400MHz, CDCI3) delta 9.26 (s, 1H), 8.17 (d, J= 6.4 Hz, 1H), 7.98 (s, 1H), 7.56-7.50 (m, 1H), 5.35-5.19 (m, 2H), 3.56-3.50 (m, 1H), 3.44-3.39 (m, 1H), 3.33 (s, 3H), 2.66 (t, J= 8.8 Hz, 1H), 2.25-2.22 (m, 1H), 2.10-2.07 (m, 1H), 1.97-1.67 (m, 6H), 1.52-1.38 (m, 7H), 1.36- 1.25 (m, 6H), 1.21 (s, 3H), 1.15-1.03 (m, 1H), 0.79 (s, 3H), 0.70 (s, 3H). LCMS Rt = 2.155 min in 4.0 min chromatography, 10-80AB, purity 100%, MS ESI calcd. For C30H44N3O3 [M+H]+ 494, found 494.

Reference： [1]Patent: WO2018/13615,2018,A1 .Location in patent: Page/Page column 130-131

52
[ 271-47-6 ]
6-(methylsulfonyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 1341 - 1349

53
[ 271-47-6 ]
[ 871792-61-9 ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 1341 - 1349

54
C₂₃H₃₇BrO₂ [ No CAS ]
[ 271-47-6 ]
1-((3R,5R,8S,9S,10R,13S,14S,17S)-3-hydroxy-3,5,10,13-tetramethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-(2H-pyrazolo[3,4-c]pyridin-2-yl)ethan-1-one [ No CAS ]
1-((3R,5R,8S,9S,10R,13S,14S,17S)-3-hydroxy-3,5,10,13-tetramethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-(1H-pyrazolo[3,4-c]pyridin-1-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.8%; 9%	With potassium carbonate; In acetone; at 25℃; for 16h;	To a mixture of I-AI (200 mg, 0.47 mmol) and K2C03 (129 mg, 0.94 mmol) in acetone (5 mL) was added lH-pyrazolo[3,4-c]pyridine (83.9 mg, 0.705 mmol) at 25C. After stirring at 25C for 16 hrs, the reaction mixture was filtered and the filtrate was concentrated in vacuum to give product which was purified by prep. HPLC, and the eluents were washed with sat.NaHCO,, dried over Na2S04, filtered and concentrated to give I-A6 (25 mg, ) and I- A7 (40 mg, ) as a solid, which were further purified by prep-TLC (DCM: Acetone = 2:3) to give pure I-A6 (4 mg, 1.8%) and I-A7 (20 mg, 9%) as a solid. (0792) [0507] I-A6: 1H NMR (400 MHz, CDCl3) d 9.26 (s, 1H), 8.19-8.14 (m, 1H), 7.98 (s, (0793) 1H), 7.55-7.50 (m, 1H), 5.35-5.18 (m, 2H), 2.70-2.61 (m, 1H), 2.29-2.09 (m, 3H), 1.84-1.71 (m, 2H), 1.55-1.40 (m, 10H), 1.38-1.35 (m, 4H), 1.31-1.22 (m, 3H), 1.20-1.11 (m, 2H), 1.08- (0794) 1.00 (m, 1H), 0.94 (s, 3H), 0.81 (s, 3H), 0.70 (s, 3H); LC-ELSD purity 99%; MS ESI calcd. for C29H42N302 [M+H]+ 464, found 464. (0795) [0508] I-A7: 1H NMR (400 MHz, CDCl3) d 8.79 (s, 1H), 8.36-8.31 (m, 1H), 8.09 (s, (0796) 1H), 7.67-7.62 (m, 1H), 5.31-5.19 (m, 2H), 2.70-2.62 (m, 1H), 2.29-2.11 (m, 3H), 1.81-1.69 (m, 2H), 1.64-1.60 (m, 1H), 1.53-1.39 (m, 9H), 1.36 (s, 3H), 1.35-1.21 (m, 4H), 1.20-1.13 (0797) (m, 2H), 1.08-1.01 (m, 1H), 0.94 (s, 3H), 0.82 (s, 3H), 0.72 (s, 3H); LC-ELSD purity 99%; MS ESI calcd. for C29H42N302 [M+H]+ 464, found 464.

Reference： [1]Patent: WO2019/126741,2019,A1 .Location in patent: Paragraph 0505-0508

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[ 271-47-6 ] Synthesis Path-Upstream 1~7

[ 271-47-6 ] Synthesis Path-Downstream 1~54

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