[ CAS No. 18184-75-3 ] {[proInfo.proName]}

Name: 18184-75-3|6-Benzyl-5,7-dihydro-5,7-dioxopyrrolo[3,4-b]pyridine|97%
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SKU: A283122
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Quality Control of [ 18184-75-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 18184-75-3 ]

SDS Specification

Alternatived Products of [ 18184-75-3 ]

Product Details of [ 18184-75-3 ]

CAS No. :	18184-75-3	MDL No. :	MFCD02930145
Formula :	C₁₄H₁₀N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DWUBVULEMQOCPO-UHFFFAOYSA-N
M.W :	238.24	Pubchem ID :	289502
Synonyms :

Calculated chemistry of [ 18184-75-3 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.07
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	69.0
TPSA :	50.27 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.57 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.82
Log Po/w (XLOGP3) :	1.66
Log Po/w (WLOGP) :	1.35
Log Po/w (MLOGP) :	1.89
Log Po/w (SILICOS-IT) :	2.32
Consensus Log Po/w :	1.81

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.72
Solubility :	0.45 mg/ml ; 0.00189 mol/l
Class :	Soluble
Log S (Ali) :	-2.33
Solubility :	1.12 mg/ml ; 0.00468 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.62
Solubility :	0.00574 mg/ml ; 0.0000241 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.82

Safety of [ 18184-75-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280	UN#:	N/A
Hazard Statements:	H302-H317	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 18184-75-3 ]

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

Upstream synthesis route of [ 18184-75-3 ]
Downstream synthetic route of [ 18184-75-3 ]

[ 18184-75-3 ] Synthesis Path-Upstream 1~13

1
[ 18184-75-3 ]
[ 5657-51-2 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 4, p. 1205 - 1210
[2] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 4, p. 1205 - 1210

2
[ 89-00-9 ]
[ 100-46-9 ]
[ 18184-75-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With silica gel In neat (no solvent) at 150℃; for 18 h; Inert atmosphere; Sealed tube	General procedure: These compounds were prepared using the same procedure as reported above, but at 150°C for 18–26h. Following work up, the crude products were purified on 15cm×2.5cm silica gel columns eluted with 60–80percent EtOAc in hexanes. The isolated yields are given in Table 3. Note: Saturated NH₄Cl was used for washing the pyridine derivatives instead of 1M HCl.
90%	With acetic anhydride In toluene at 30 - 60℃;	In a flask 120g2,3- pyridinedicarboxylic acid, 110g of acetic anhydride, heated up with stirring, the solid is gradually dissolved, and when the internal temperature reached 92 deg.] C, all the solid had dissolved, 92 ~ 95 temperature control for 2 to 3 hours to 2, 3-pyridyl acid ≤0.1percent, the reaction was completed, cooling to 50 ~ 60 , evaporated under reduced pressure, heated to 80 ~ 85 , no flow to continue evaporated under reduced pressure, cooling to 50 ~ 60 , toluene was added 40g , mixing temperature, the toluene was evaporated to dryness under reduced pressure, 40g of toluene and then once with the above-described method, steaming complete, 169g of toluene was added, heated to 40 ~ 50 stir, cooled to 30 ~ 40 benzylamine was slowly added dropwise 92.3g dropping process control temperature does not exceed 55 ,2 hours drop end, at a temperature of 40 ~ 50 for 3 to 4 hours to pyridine-2,3-dicarboxylic acid anhydride ≤0.1percent, the reaction was completed, water bath heating, external temperature control 85 evaporated to dryness under reduced pressure, the residue was added 110g acetic anhydride, heated up with stirring, the temperature control 92 ~ 95 for 1 to 2 hours to precipitate solid, and stirring was continued for 1 to 2 hours to ring-opened product ≤0.1percent, the reaction was completed, cooling to 50 ~ 60 distilled off under reduced pressure dry, warmed to 80 ~ 85 , no flow to continue distilled off under reduced pressure, temperature lowered to room temperature, was added 200mL95percent ethanol, cooled to 0 stirred for 5 hours, filtered, cooled to 5 cake was washed with 95percent ethanol and washed 28mLx3 three times, drained, dried in vacuo to give an off-white solid 6-benzyl-pyrrolo [3,4-b] pyridine-5,7-dione 150g, yield 88 ~ 90percent

Reference： [1] Tetrahedron, 2015, vol. 71, # 48, p. 9101 - 9111
[2] Patent: CN105777750, 2016, A, . Location in patent: Paragraph 0024; 0025; 0040
[3] Asian Journal of Chemistry, 2013, vol. 25, # 15, p. 8701 - 8707

3
[ 100872-65-9 ]
[ 18184-75-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	With acetic anhydride; trifluoroacetic acid In toluene at 100 - 110℃;	Preparation 646-Benzyl-5H-pyrrolo[3, 4-blpyridine-5, 7(6H)-dione; To 2-(benzylcarbamoyl)nicotinic acid (Preparation 63) (202.7 g, 0.789 mol) was added acetic anhydride (30OmL), toluene (30OmL) and trifluoro-acetic acid (3OmL) successively. Then the mixture was heated to 100-110⁰C and stirred at this temperature overnight. Another portion of toluene (20OmL) was added. Then the mixture was cooled to O⁰C slowly. The solid formed in the mixture was filtered, washed with toluene (15OmL) and dried in vacuo to afford the title compound as an off-white solid (153.4 g 81 percent).

Reference： [1] Patent: WO2010/131145, 2010, A1, . Location in patent: Page/Page column 79-80
[2] South African Journal of Chemistry, 2012, vol. 65, p. 53 - 61

4
[ 4664-00-0 ]
[ 100-39-0 ]
[ 18184-75-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine In N,N-dimethyl-formamide at 40℃; for 2 h;	To 1000 ml three-necked flask were added 148 g pyrrolo[3,4-b]pyridine-5,7-dione (1.0 mol) and 500 ml of N,N-dimethylformamide was dissolved, 110 g of triethylamine was added (1.1 mol) was heated to 40 °C, was slowly added dropwise 188 g of benzyl bromide (1.1 mol), stirred at 40 °C incubated for 2 hours, the reaction compound into a dark brown liquid, TLC tracking reaction when raw pyrrolo[3,4-b]pyridine-5,7-dione completion of the reaction, the reaction mixturewas cooled to room temperature with stirring, the reaction mixture was cooled as slowly poured into 500 ml of cold water, alarge number of off-white solid immediately precipitated, was filtered, The filter cake was washed with cold water, and driedovernight at 60 °C under vacuum to give 214 g white powder in a yield of 90percent.

Reference： [1] Patent: CN102746294, 2016, B, . Location in patent: Paragraph 0069; 0070

5
[ 699-98-9 ]
[ 100-46-9 ]
[ 18184-75-3 ]

Yield	Reaction Conditions	Operation in experiment
57%	for 18 h; Heating / reflux	Preparation 31 : 6-Benzyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione.Benzylamine (3.85 ml, 35.2 mmol) was added to a suspension of 2,3-pyridinedicarboxylic anhydride (5 g, 33.5 mmol), in acetic acid (50 ml), and the mixture was heated under reflux for 18 hours. It was then cooled to room temperature, concentrated in vacuo and the residue was triturated with diethyl ether to afford the title compound as a white solid in 57percent yield, 4.52 g. 1HNMR(400MHz, CDCI3) δ: 4.79(s, 2H), 7.27(m, 1H), 7.32(m, 4H), 7.78(dd, 1H), 8.29(d, 1H), 8.96(d, 1H); LRMS APCI m/z 239 [M+H]+
56%	Reflux	A solution of compound 6a (5.0 g, 33.6 mol) and compound 6b (3.9 g, 36.9 mmol) in AcOH (60 ml) was refluxed overnight. The reaction was concentrated and purified by silica gel chromatography (eluting with petroleum ether/EtOAc=10:1~3:1) to give compound 6c (4.5 g, yield:56percent). 1H NMR (400MHz,CHLOROFORM-d) δ= 8.16 (dd, J=1.3, 7.7 Hz, 1H), 7.61 (dd, J=5.0, 7.7 Hz, 1H), 7.46 (d,J=6.8 Hz, 2H), 7.36 - 7.31 (m, 3H), 7.29 (d, J=6.6 Hz, 2H), 4.92 (s, 2H)
12 g	at 45℃; for 1 h;	Pyridine-2,3-dicarboxylic acid (10.0 g, 59.9 mmol) and acetic anhydride (15 mL) were added successively to toluene (20 mL) in the three-necked flask and the mixture was stirred at 110 °C for 3 h. After cooling to room temperature, sodium acetate (0.1 g) was added and benzylamine (7.05 g, 65.9 mmol) was dropped in below 45 °C with stirring. The mixture was retained at 45 °C for 1 h and acetic anhydride (10 mL) was poured in with stirring for 2 h under reflux. The solvent was removed under vacuum and water (40 mL) was added with stirring for 30 min. After filtration, the precipitate was washed with water (3×20 mL) and ethanol (3×10 mL) respectively and it was dried at 50 °C under vacuum to give the title compound (12.0 g, 84.2percent yield)

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 14, p. 4159 - 4162
[2] Heterocycles, 2002, vol. 57, # 10, p. 1881 - 1890
[3] European Journal of Medicinal Chemistry, 2007, vol. 42, # 5, p. 614 - 626
[4] Chinese Journal of Chemistry, 2015, vol. 33, # 11, p. 1269 - 1275
[5] Organic Letters, 2018, vol. 20, # 18, p. 5610 - 5613
[6] Patent: WO2006/123242, 2006, A1, . Location in patent: Page/Page column 39;40
[7] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 6, p. 1458 - 1462
[8] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 6, p. 1757 - 1763
[9] Patent: WO2009/125425, 2009, A2, . Location in patent: Page/Page column 6; 9
[10] South African Journal of Chemistry, 2012, vol. 65, p. 53 - 61
[11] Synthetic Communications, 2017, vol. 47, # 3, p. 238 - 244

6
[ 4664-00-0 ]
[ 100-46-9 ]
[ 18184-75-3 ]

Reference： [1] European Journal of Medicinal Chemistry, 2007, vol. 42, # 5, p. 614 - 626
[2] Advanced Synthesis and Catalysis, 2015, vol. 357, # 5, p. 1013 - 1021

7
[ 89-00-9 ]
[ 100-46-9 ]
[ 18184-75-3 ]

Reference： [1] Patent: US5654318, 1997, A,

8
[ 89-00-9 ]
[ 18184-75-3 ]

Reference： [1] Heterocycles, 2002, vol. 57, # 10, p. 1881 - 1890
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 6, p. 1757 - 1763
[3] South African Journal of Chemistry, 2012, vol. 65, p. 53 - 61
[4] Advanced Synthesis and Catalysis, 2015, vol. 357, # 5, p. 1013 - 1021
[5] Chinese Journal of Chemistry, 2015, vol. 33, # 11, p. 1269 - 1275
[6] Synthetic Communications, 2017, vol. 47, # 3, p. 238 - 244
[7] Patent: CN102746294, 2016, B,

9
[ 699-98-9 ]
[ 100-46-9 ]
[ 2503-55-1 ]
[ 18184-75-3 ]

Reference： [1] Heterocycles, 2002, vol. 57, # 10, p. 1881 - 1890

10
[ 24195-07-1 ]
[ 18184-75-3 ]

Reference： [1] South African Journal of Chemistry, 2012, vol. 65, p. 53 - 61

11
[ 81335-71-9 ]
[ 100-46-9 ]
[ 18184-75-3 ]

Reference： [1] South African Journal of Chemistry, 2012, vol. 65, p. 53 - 61

12
[ 18184-75-3 ]
[ 159877-36-8 ]

Reference： [1] Patent: WO2013/71697, 2013, A1,
[2] Patent: US2014/228361, 2014, A1,
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 6, p. 1458 - 1462

13
[ 18184-75-3 ]
[ 5654-94-4 ]

Reference： [1] Patent: CN102746294, 2016, B,

[ 18184-75-3 ] Synthesis Path-Downstream 1~10

1
[ 4664-00-0 ]
alkyl halide [ No CAS ]
[ 18184-75-3 ]

Reference： [1]Heterocycles,2002,vol. 57,p. 1881 - 1890

2
[ 4664-00-0 ]
[ 100-46-9 ]
[ 18184-75-3 ]

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 614 - 626
[2]Advanced Synthesis and Catalysis,2015,vol. 357,p. 1013 - 1021

3
[ 18184-75-3 ]
[ 5657-51-2 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 1205 - 1210
[2]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 1205 - 1210

4
[ 18184-75-3 ]
[ 128740-13-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 5%-palladium/activated carbon; hydrogen In tetrahydrofuran at 100℃; for 10h;	6-Benzyltetrahydro-1H-pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione (5) Mixture of compound 4 (10.0 g), 5% Pd/C (1.0 g) and tetrahydrofuran (200 mL) was heated to 100 °C under hydrogen atmosphere in autoclave at a pressure of 3.5 MPa for 10 h. After cooling to room temperature, Pd/C was filtered out immediately, and the filtrate was concentrated to yield the light yellow oil (10.2 g, 99.0% yield, 96.4% purity).
90%	With ruthenium-carbon composite; hydrogen
90%	With 5%-palladium/activated carbon In tetrahydrofuran at 80 - 90℃; for 8h;	6 preparation of 6-benzyloctahydropyrrolo[3,4-b]pyridine-5,7-dione To 2000 ml autoclave was charged with 238 g of 6-benzylpyrrolo[3,4-b]pyridine-5,7-dione (1.0 mol) and 24 g of 5% palladium on carbon, 1,000 ml of tetrahydrofuran was added, in at 80-100 atmospheres, stirring at 80-90 °C for 8 hours reaction mixture turns bright yellow liquid, TLC the reaction was followed, when the starting material of 6-benzylpyrrolo[3,4-b]pyridine-5,7-done at the conclusion of the reaction, the reaction mixture was cooled to room temperature, filtered, the filter cake washed with 500 ml oftetrahydrofuran, combined tetrahydrofuran, the solvent removed under reduced pressure to give a yellow solid 219.6 g, 90% yield.

85%	Stage #1: 6-benzyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione With palladium 10% on activated carbon; hydrogen In toluene at 87 - 93℃; for 2.5h; Autoclave; Inert atmosphere; Stage #2: In isopropyl alcohol; toluene at 20 - 60℃; for 6h; Inert atmosphere;	S2, catalytic hydrogenation: Was added 400mL of toluene in an autoclave, the amine compound 100g, 10% Pd / C5g, nitrogen pressure to 5kg / cm2, held 30 minutes, the autoclave was detected good air tightness, purged with nitrogen three times, purged with hydrogen 3 times to 200rpm stirring was pressurized with hydrogen to 20kg / cm2, a hydrogen off, temperature was raised to 90 deg.] C, the temperature stability up hydrogen to 30kg / cm2, the hydrogenation mixture was stirred until the pressure was reduced 20 ~ 25kg / cm2, and a hydrogen to fill 35 ~ 40kg / cm2 for continued until the hydrogen absorption up to no hydrogen, and stirring was continued at 87 ~ 93 2 hours the hydrogenation was completed, cooling to 20 ~ 25 , nitrogen pressure filtration, rinsed with toluene 5g Pd / C once, Pd / C apply recovered filtrate water bath, vacuum recovery toluene to dryness, cooling to room temperature, isopropanol 200L, heated to 50 ~ 60 clear solution was stirred,Cooled to -5 ~ 0 crystallization for 6 hoursFiltered, the filter cake rinsed with cold isopropanol 10gx2 2 times, drained, and dried in vacuo hydride6-Benzyl - hexahydro - pyrrolo [3,4.b] pyridine-5,7-dione82 ~ 87g, yield 80 ~ 85%,
85.4%	With palladium on activated charcoal; hydrogen In tetrahydrofuran; methanol at 60℃;	6-benzyltetrahydro-1H-pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione (6d) A suspension of compound 6c (4 g, 16.8 mmol) and Pd/C (400 mg) in MeOH and THF(1:1, 40 ml) was stirred at 60°C under 50Psi of hydrogen atmosphere overnight. The reaction mixture was filtered and the filtrate was concentrated by rotary evaporation. The residue was purified by silica gel chromatography (eluting with petroleum ether/EtOAc=10:1~1:1) to give compound 6d (3.5 g, yield: 85.4%). 1H NMR (400MHz, CHLOROFORM-d) δ=7.39 - 7.34 (m, 2H), 7.34 - 7.30 (m, 2H), 7.29 (d,J=2.4 Hz, 1H), 4.67 (s, 2H), 3.86 (d, J=7.1 Hz, 1H), 2.88 (q, J=7.1 Hz, 1H), 2.84 -2.77 (m, 1H), 2.68 (td, J=5.9, 11.6 Hz, 1H), 2.03 - 1.94 (m, 1H), 1.66 - 1.61 (m, 1H),1.53 (m, 2H)
60%	With palladium 10% on activated carbon; hydrogen In 2-methoxy-ethanol at 90℃; for 6h;	25.1 6-benzyltetrahvdro-l H-pyrrolor3.4-blpyridine-5.7(6H,7aH)-dione To a solution of 6-benzyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)- dione (5.00 g) in glycol monomethyl ether was added a catalytic amount of 10 % Pd/C. The reaction mixture was heated to 90 °C and stirred for 6 h under H2, then cooled to rt. The resulted mixture was poured into 100 mL of water and extracted with CH2C12 (50 mLx3). The combined organic phases were dried over anhydrous Na2S04 and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 1 :2 (v/v) PE/EA) to give the title compound as colorless oil (3.00 g, 60.00 %), HPLC: 95.00 %. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 245.1 (?+1);? NMR (400 MHz, CDC13) ?: 1.47-1.53 (m, 4H), 2.12 (s, l H), 2.63-2.69 (m, 1 H), 2.76-2.88 (m, 2H), 3.83 (d, 7 = 8.2, 2H), 4.64 (s, 1 H), 7.25-7.36 (m, 5H) ppm.
60%	With palladium 10% on activated carbon; hydrogen In 2-methoxy-ethanol at 90℃; for 6h;	25.1 6-benzyltetrahydro-1H-pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione To a solution of 6-benzyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione (5.00 g) in glycol monomethyl ether was added a catalytic amount of 10% Pd/C. The reaction mixture was heated to 90° C. and stirred for 6 h under H2, then cooled to rt. The resulted mixture was poured into 100 mL of water and extracted with CH2Cl2 (50 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 1:2 (v/v) PE/EA) to give the title compound as colorless oil (3.00 g, 60.00%), HPLC: 95.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 245.1 (M+1); 1H NMR (400 MHz, CDCl3) δ: 1.47-1.53 (m, 4H), 2.12 (s, 1H), 2.63-2.69 (m, 1H), 2.76-2.88 (m, 2H), 3.83 (d, J=8.2, 2H), 4.64 (s, 1H), 7.25-7.36 (m, 5H) ppm.
58%	With palladium 10% on activated carbon; hydrogen at 90℃; for 6h;
	In 2-methoxy-ethanol	R.7 6-Benzyl-5,7-dioxo-octahydropyrrolo[3.4-b]pyridine REFERENCE EXAMPLE 7 6-Benzyl-5,7-dioxo-octahydropyrrolo[3.4-b]pyridine To 10 g of 6-benzyl-5,7-dihydro-5,7-dioxopyrrolo[3.4-b]pyridine were added 84 ml of 2-methoxyethanol and 1.5 g of a ruthenium-on-carbon catalyst, and hydrogenation was conducted under a pressurized hydrogen gas atmosphere at 4.5 kg/cm2 for 22 hours. The catalyst was removed by filtration, and the filtrate was concentrated. To the concentrate were added 84 ml of 2-methoxyethanol and 2 g of a palladium-on-charcoal catalyst, and hydrogenation was conducted under a pressurized hydrogen gas atmosphere at 4.5 kg/cm2 for 7 hours. The catalyst was removed by filtration, and the filtrate was concentrated to yield 10.4 g of the titled compound. Throughout the hydrogenation, the reaction vessel was heated by a tungsten lamp. 1 H-NMR (400 MHz, CDCl3) δ ppm: 1.52 (2H, dt, J=11.8, 5.9Hz), 1.65 (1H, dt, J=6.8, 13.4Hz), 1.97 (1H, dt, J=5.9, 13.4Hz), 2.68 (1H, dt, J=11.8, 5.9Hz), 2.79 (1H, dt, J=11.8, 5.9Hz), 2.86 (1H, dd, J=6.8, 7.3Hz), 3.85 (1H, d, J=7.3Hz), 4.65 (2H, s), 7.26-7.34 (5H, m)
	With hydrogen In methanol at 55 - 60℃; for 7h; Inert atmosphere; Autoclave;	2 5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione (72.48g, 0.3045mole) in methanol (217.44ml) was charged with 5% Pd/C (7.24 g) under nitrogen atmosphere in an autoclave. The reaction vessel was evacuated followed by application of Hydrogen gas at a pressure of 4.0-4.5 kg/cm2. The reaction mixture was heated at a temperature of 55-600C for a period of 7 hours. The reaction mixture was filtered and then washed with methanol. The solvent was distilled off completely under vacuum below 45°C.
	With 5%-palladium/activated carbon; hydrogen In methanol at 90℃; for 8h; Autoclave;

Reference： [1]Chen, Shipeng; Liu, Dongqi; Si, Leilei; Chen, Ligong; Yan, Xilong [Synthetic Communications, 2017, vol. 47, # 3, p. 238 - 244]
[2]Reddy, G. Prashanth; Bandichhor, Rakeshwar [Asian Journal of Chemistry, 2013, vol. 25, # 15, p. 8701 - 8707]
[3]Current Patent Assignee: Guo Feng; Guo, Feng - CN102746294, 2016, B Location in patent: Paragraph 0071; 0072
[4]Current Patent Assignee: JIANGXI ZHONGDE INTEGRITY TECH; JIANGXI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE - CN105777750, 2016, A Location in patent: Paragraph 0026; 0027; 0028; 0040
[5]Wu, Songliang; Sun, Yu; Hu, Yi; Zhang, Hongmei; Hou, Lijuan; Liu, Xing; Li, Yufeng; He, Haiying; Luo, Zhi; Chen, Yuan; Wang, Yuhe; Shi, Weihua; Shen, Liang; Cao, Changqing; Liang, Wei; Xu, Qing; Lv, Qiang; Lan, Jiong; Li, Jian; Chen, Shuhui [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 6, p. 1458 - 1462]
[6]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - WO2013/71697, 2013, A1 Location in patent: Paragraph 00310
[7]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - US2014/228361, 2014, A1 Location in patent: Paragraph 0479-0480
[8]Ding, Guangni; Lu, Bin; Li, Yuyuan; Wan, Jun; Zhang, Zhaoguo; Xie, Xiaomin [Advanced Synthesis and Catalysis, 2015, vol. 357, # 5, p. 1013 - 1021]
[9]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - US5654318, 1997, A
[10]Current Patent Assignee: NEULAND LABORATORIES LTD - WO2009/125425, 2009, A2 Location in patent: Page/Page column 6; 9
[11]Liu, Jingbo; Li, Yuxin; Chen, Youwei; Hua, Xuewen; Wan, Yingying; Wei, Wei; Song, Haibin; Yu, Shujing; Zhang, Xiao; Li, Zhengming [Chinese Journal of Chemistry, 2015, vol. 33, # 11, p. 1269 - 1275]

5
[ 18184-75-3 ]
[ 109966-30-5 ]

Yield	Reaction Conditions	Operation in experiment
51%	With lithium aluminium tetrahydride In diethyl ether at 20℃; for 3h;	Preparation 32: 6-Benzyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine.Lithium aluminium hydride (1M in diethyl ether, 37.8 ml, 37.8 mmol) was added dropwise to a suspension of the product of preparation 31 (4.5 g, 18.9 mmol), in diethyl ether (45 ml), and the mixture was stirred at room temperature for 3 hours. It was then cooled to O°C, quenched with saturated sodium sulfate solution (50 ml) and diluted with dichloromethane (50 ml). The mixture was then filtered through Celite washing through with diethyl ether (50 ml) and dichloromethane (50 ml). The filtrate layers were separated and the organic solution was concentrated in vacuo. Purification of the residue by Golumn chromatography on silica gel, eluting with dichloromethane:methanol, 95:5, afforded the title compound in 51 % yield, 2.02 g.1HNMR(400MHz, CD3OD) δ: 3.94(s, 4H), 3.98(s, 2H), 7.36(m, 6H), 7.68(d, 1 H), 8.32(d, 1H); LRMS APCI m/z 211 [M+H]+
20%	Stage #1: 6-benzyl-5H-pyrrolo[3,4–b]pyridine-5,7(6H)-dione With lithium aluminium tetrahydride In tetrahydrofuran Reflux; Stage #2: With water; sodium hydroxide In tetrahydrofuran at 0℃;	65 Preparation 656-Benzyl-6,7-dihvdro-5H-pyrrolo[3,4-blpyridine; To a refluxing suspension of lithium aluminium hydride (24.5 g, 0.645 mol) in dry tetrahydrofuran (30OmL) was added a suspension of 6-benzyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione (Preparation 64, 76.8 g, 0.322 mol) in dry tetrahydrofuran (40OmL) with vigorous stirring. After the addition of the 6-benzyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione was complete, the mixture was stirred for another 20 minutes. The mixture was cooled to O0C and quenched with 15% aqueous sodium hydroxide solution and stirred for 1 hour. The mixture was filtered, washed with ethyl acetate (12OmL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (gradient elution 80:1 to 40:1 ) to afford the title compound as an orange liquid (13.8 g, 20%).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2006/123242, 2006, A1 Location in patent: Page/Page column 40
[2]Current Patent Assignee: PFIZER INC - WO2010/131145, 2010, A1 Location in patent: Page/Page column 80

6
[ 24195-07-1 ]
[ 18184-75-3 ]

Reference： [1]South African Journal of Chemistry,2012,vol. 65,p. 53 - 61

7
[ 18184-75-3 ]
[ 159877-36-8 ]

Reference： [1]Patent: WO2013/71697,2013,A1
[2]Patent: US2014/228361,2014,A1
[3]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1458 - 1462

8
[ 18184-75-3 ]
[ 151213-40-0 ]

Reference： [1]Asian Journal of Chemistry,2013,vol. 25,p. 8701 - 8707
[2]Patent: CN105777750,2016,A
[3]Synthetic Communications,2017,vol. 47,p. 238 - 244

9
[ 147-71-7 ]
[ 18184-75-3 ]
[ 151434-04-7 ]

Yield	Reaction Conditions	Operation in experiment
45 g	Stage #1: 6-benzyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione With palladium on activated charcoal; hydrogen In methanol at 60℃; Autoclave; Stage #2: D-tartaric acid In methanol; acetone at 20℃; for 5h;	4 Example 4: Preparation of (4aR,7aS)-6-benzyltetrahydro-1H-pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione mono tartarate salt represented by Formula-7 To an autoclave was added lOOg (0.42mol) of 6-benzyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)- dione and 300ml of methanol followed by addition of catalyst, Pd/C. The reaction mass was then stirred under hydrogen pressure of 20-25 Kg/cm2 at 60°C till completion of reaction. Filtered the reaction mass and added 1000ml of acetone to the methanol layer so obtained followed by addition of 52.25g (0.35mol) of D(-)-tartaric acid to get the clear solution. The reaction mass was then allowed to cool at room temperature and stirred for 5h. Filtration was carried to get solid compound. Dissolved the solid so obtained in 85% aq. isopropyl alcohol and heated to reflux to get clear solution. Cooled the reaction mass to room temperature followed by filtration to get 45g of (4aR,7aS)-6-benzyltetrahydro-lH-pyrrolo[3,4-b]pyridine- 5,7(6H,7aH)-dione mono tartarate salt.It can be observed that in accordance with the teachings of present invention, the process of preparation of compound of Formula- 7 is done without isolation of intermediate, (4aR,7aS)- 6-benzyltetrahydro-lH-pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione, by effectively using the leftover solvent of catalytic de-aromatization process like methanol, to get (4aR,7aS)-6- benzyltetrahydro-lH-pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione mono tartarate salt which is contrary to the understanding from prior art wherein, (4aR,7aS)-6-benzyltetrahydro-lH- pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione firstly, is isolated by distillation of methanol, which is discarded, and then resolution is performed using an acid in a solvent system. This aspect of present invention provides advantages such as (a) evading not merely number of additional process steps but also wastage of solvents like methanol; (b) enabling the reaction to be conducted in an in situ manner; (c) making the process easier for commercial adoption.

Reference： [1]Current Patent Assignee: MANKIND RESEARCH CENTRE - WO2014/97272, 2014, A2 Location in patent: Page/Page column 21-22

10
[ 4664-00-0 ]
[ 100-39-0 ]
[ 18184-75-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine; In N,N-dimethyl-formamide; at 40℃; for 2.0h;	To 1000 ml three-necked flask were added 148 g pyrrolo[3,4-b]pyridine-5,7-dione (1.0 mol) and 500 ml of N,N-dimethylformamide was dissolved, 110 g of triethylamine was added (1.1 mol) was heated to 40 C, was slowly added dropwise 188 g of benzyl bromide (1.1 mol), stirred at 40 C incubated for 2 hours, the reaction compound into a dark brown liquid, TLC tracking reaction when raw pyrrolo[3,4-b]pyridine-5,7-dione completion of the reaction, the reaction mixturewas cooled to room temperature with stirring, the reaction mixture was cooled as slowly poured into 500 ml of cold water, alarge number of off-white solid immediately precipitated, was filtered, The filter cake was washed with cold water, and driedovernight at 60 C under vacuum to give 214 g white powder in a yield of 90%.

Reference： [1]Patent: CN102746294,2016,B .Location in patent: Paragraph 0069; 0070

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[ 18184-75-3 ] Synthesis Path-Upstream 1~13

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Aryls

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