[ CAS No. 1609071-04-6 ] {[proInfo.proName]}

Name: 1609071-04-6|5,6-Bis((4-methoxybenzyl)oxy)isobenzofuran-1,3-dione|95+%
Brand: Ambeed
SKU: A112412
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Quality Control of [ 1609071-04-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1609071-04-6 ]

CAS No. :	1609071-04-6	MDL No. :	MFCD27998182
Formula :	C₂₄H₂₀O₇	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BLMQFZDSZGKYFR-UHFFFAOYSA-N
M.W :	420.41	Pubchem ID :	86280376
Synonyms :

Safety of [ 1609071-04-6 ]

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

Application In Synthesis of [ 1609071-04-6 ]

* 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 [ 1609071-04-6 ]
Downstream synthetic route of [ 1609071-04-6 ]

[ 1609071-04-6 ] Synthesis Path-Upstream 1~4

1
[ 1609071-03-5 ]
[ 1609071-04-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With Jones reagent In acetone at 0℃; for 1 h;	The total amount (42.71 g, 79 mmol) of Compound 1d obtained was suspended in acetone (350 mL)Next, Jones reagent (2.67 mol / L, 71.0 mL, 190 mmol) was added thereto at 0 °C. The mixture was stirred at 0 ° C. for 1 hour. After diluting the reaction mixture with dichloromethane and water,Sodium bisulfite was added at 0 ° C.The resulting solution was then separated, washed with water and saturated salt solution and dried over magnesium sulfate. After filtering off the magnesium sulfate, the liquid was concentrated under reduced pressure. Next, the precipitated solid was collected by filtration and washed with diisopropyl ether to obtain Compound 1e (26.94 g, 81percent)
26.94 g	With Jones reagent In acetone at 0℃; for 1 h; Inert atmosphere	The total amount of compound Id yielded (42.71 g, 79 mmol) was suspended into acetone (350 mL) , and thereto was then added Jone' s reagent (2.67 mol/L, 71.0 mL, 190 mmol) at 0°C. The mixture was stirred at 0°C for 1 hour. The reaction mixture was diluted with dichloromethane and water, then added sodium bisulfite at 0°C. The resultant solution was then separated and washed with water and a saturated salt solution, and dried over magnesium sulfate. Magnesium sulfate was filtrated off, and then the liquid was concentrated under reduced pressure. The precipitated solid was then collected by filtration, and washed with diisopropyl ether to yield compound le (26.94 g, 81percent). ¹H-NMR (CDCI₃) δ: 7.38 (2H, s) , 7.35 (4H, d, J = 8.1 Hz), 6.92 (4H, d, J = 8.1 Hz), 5.21 (4H, s) , 3.82 (6H, s) .

Reference： [1] Patent: JP6377570, 2018, B2, . Location in patent: Paragraph 0299; 0303
[2] Patent: WO2014/68388, 2014, A1, . Location in patent: Paragraph 0228

2
[ 531-88-4 ]
[ 1609071-04-6 ]

Reference： [1] Patent: WO2014/68388, 2014, A1,
[2] Patent: JP6377570, 2018, B2,

3
[ 53766-43-1 ]
[ 1609071-04-6 ]

Reference： [1] Patent: WO2014/68388, 2014, A1,
[2] Patent: JP6377570, 2018, B2,

4
[ 1609071-02-4 ]
[ 1609071-04-6 ]

Reference： [1] Patent: WO2014/68388, 2014, A1,
[2] Patent: JP6377570, 2018, B2,

[ 1609071-04-6 ] Synthesis Path-Downstream 1~22

1
[ 13562-40-8 ]
[ 1609071-04-6 ]
[ 1609071-16-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	In ethanol; at 20℃; for 24h;Inert atmosphere;	Compound le (1.88 g, 4.5 mmol) was dissolved into ethanol (10 mL) , and thereto was then added Compound 4a (0.58 g, 4.5 mmol) . The mixture was stirred at rt for 1 day. The precipitated solid was then collected by filtration, and washed with ethanol and diisopropyl ether to yield compound 4b (2.00 g, 84%). ^-NMR (CDCI3) delta: 7.80 (1H, s), 7.32 (2H, d, J = 8.5 Hz), 7.08 (2H, d, J = 8.5 Hz), 6.73 (2H, d, J = 8.5 Hz), 6.69 (2H, d, J = 8.5 Hz), 6.49 (1H, br s), 5.01 (2H, s) , 4.65 (2H, s), 4.35 (2H, br s), 3.78 (3H, s) , 3.76 (3H, s), 3.27-3.01 (6H, br m) , 1.90 (4H, br s) .
84%	In ethyl [2]alcohol; at 20℃; for 24h;	Compound 1e (1.88 g, 4.5 mmol) was dissolved in ethanol (10 mL), and then compound 4 a (0.58 g, 4.5 mmol) was added thereto. The mixture was stirred at room temperature for 1 day. Next, the precipitated solid was collected by filtration and washed with ethanol and diisopropyl ether to obtain compound 4b (2.00 g, 84%).

Reference： [1]Patent: WO2014/68388,2014,A1 .Location in patent: Paragraph 0245
[2]Patent: JP6377570,2018,B2 .Location in patent: Paragraph 0320; 0321

2
[ 1609071-18-2 ]
[ 1609071-04-6 ]
[ 1609071-19-3 ]

Yield	Reaction Conditions	Operation in experiment
68%	In ethanol; at 20 - 80℃; for 30h;Inert atmosphere;	Compound le (2.10 g, 5.0 mmol) was dissolved into ethanol (10 mL) , and thereto was then added Compound 5b (0.65 g, 5.0 mmol). The mixture was stirred at rt for 1 day, 50C for 2 hours and 80C for 4 hours. The precipitated solid was then collected by filtration, and washed with ethanol and diisopropyl ether to yield compound 5c (1.81 g, 68%). """H-NMR (CDCla) delta: 7.69 (1H, s) , 7.61 (1H, s), 7.39-7.36 (4H, m) , 6.92-6.89 (4H, m) , 5.23 (2H, s) , 5.19 (2H, s), 4.19 (2H, t, J = 6.7 Hz), 3.81 (6H, s) , 2.90 (2H, br s), 2.60 (4H, br s), 1.77 (4H, br s) .
68%	In ethyl [2]alcohol; at 20 - 80℃;	Compound 1e (2.10 g, 5.0 mmol) was dissolved in ethanol (10 mL), and then compound 5 b (0.65 g, 5.0 mmol) was added thereto. The mixture was stirred at room temperature for 1 day, at 50 C. for 2 hours, and at 80 C. for 4 hours. Next, the precipitated solid was collected by filtration and washed with ethanol and diisopropyl ether to obtain compound 5c (1.81 g, 68%).

Reference： [1]Patent: WO2014/68388,2014,A1 .Location in patent: Paragraph 0249
[2]Patent: JP6377570,2018,B2 .Location in patent: Paragraph 0323; 0325

3
[ 1609071-62-6 ]
[ 1609071-04-6 ]
[ 1609071-63-7 ]

Yield	Reaction Conditions	Operation in experiment
57%		The entire amount of the obtained compound 26b was dissolved in toluene (40 mL), and the solution was cooled with ice. Compound 26c (4.20 g, 10 mmol) was added thereto. After stirring at room temperature for 1 hour and then stirring under reflux for 6 hours, an aqueous sodium hydroxide solution was added to the reaction mixture, followed by extraction with ethyl acetate. The inorganic substance was filtered off and then concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate / 3% triethylamine in hexane) to give compound 26d as a white solid. Yield: 3.60 g (57%)
3.6 g		A solution of Compound 26a (1.29 g, 10 mmol) in ethanol (10 mL) was cooled with ice, and thereto was added B0C2O solution (2.44 mL, 10.5 mmol) in ethanol (10 mL) dropwise. After stirring at room temperature for over night, the reaction mixture was concentrated and subsequently drying under reduced pressure to yield Compound 26b as colorless oil. The obtained Compound 26b was used in the next reaction without purification. The total amount of Compound 26b yielded was dissolved in toluene (40 mL) , and the solution was cooled with ice. Thereto was added Compound 26c (4.20 g, 10 mmol) . After stirring at room temperature for 1 hour, then stirring at reflux for 6 hours, aqueous sodium hydroxide was added to the reaction mixture, followed by extraction with ethyl acetate. The inorganic substance was removed by filtration, and then concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (3% triethylamine in ethyl acetate/hexane) to yield Compound 26d as a white solid. Yielded amount: 3.60 g (57%) ^-NMR (CDCI3) delta: 1.51 (4H, s), 1.56 (9H, s) , 2.42-2.46 (4H, m) , 2.71 (2H, q, J= 7.24 Hz), 3.71-3.79 (2H, m) , 3.82 (6H, s) , 5.18 (4H, s) , 6.89-6.92 (4H, m) , 7.33-7.37 (6H, m) .

Reference： [1]Patent: JP6377570,2018,B2 .Location in patent: Paragraph 0394; 0396
[2]Patent: WO2014/68388,2014,A1 .Location in patent: Paragraph 0310

4
[ 1609071-04-6 ]
[ 1123-05-3 ]
[ 1609071-64-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	With acetic acid; In toluene; for 1h;Inert atmosphere; Cooling with ice; Reflux;	A solution of Compound 27a (911 mg, 7.0 mmol) in toluene (30 mL) was cooled with ice, and thereto was added Compound 26c (2.94 g, 7.0 mmol) . After stirring at room temperature for 30 minutes, thereto was added acetic acid (440 L, 7.7 mmol) . After stirring at reflux for 1 hour, aqueous sodium hydroxide was added to the reaction mixture, followed by extraction with ethyl acetate. The inorganic substance was removed by filtration, and then concentrated under reduced pressure. Thereto was added diisopropyl ether to precipitate a solid. The solid was collected by filtration, so as to yield compound 27b as a white solid. Yielded amount: 2.60 g (70%) 1H-NMR (CDC13) delta: 1.71-1.74 (4H, m) , 2.58 (4H, s), 2.89 (2H, t, J= 5.71 Hz), 3.81 (6H, s), 4.29 (2H, t, J= 5.71 Hz), 5.17 (4H, s), 6.90 (4H, d, J = 8.66 Hz), 7.32 (2H, s) , 7.34 (4H, d, J = 8.66 Hz) .
70%		A solution of compound 27a (911 mg, 7.0 mmol) in toluene (30 mL) was cooled with ice and compound 26 c (2.94 g, 7.0 mmol) was added thereto. After stirring at room temperature for 30 minutes, acetic acid (440 muL, 7.7 mmol) was added thereto. After stirring for 1 hour under reflux, an aqueous sodium hydroxide solution was added to the reaction mixture, followed by extraction with ethyl acetate. The inorganic substance was filtered off and then concentrated under reduced pressure. To this was added diisopropyl ether to precipitate a solid. The solid was collected by filtration, whereby Compound 27b was obtained as a white solid.Yield: 2.60 g (70%)

Reference： [1]Patent: WO2014/68388,2014,A1 .Location in patent: Paragraph 0312
[2]Patent: JP6377570,2018,B2 .Location in patent: Paragraph 0398; 0399

5
[ 1609071-04-6 ]
[ 60-34-4 ]
[ 1609072-22-1 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 20℃; for 1.5h;Inert atmosphere; Reflux;	Compound 110a (2.10 g, 5.00 mmol) was dissolved into ethanol (20 mL) , and thereto was then added methyl hydrazine (0.28 ml, 5.25 mmol) . The mixture was stirred at rt for 30 minutes, then reflux for 1 hour. The reaction mixture was evaporated. The precipitated solid was then collected by filtration, and washed with diisopropyl ether to yield compound 110b (2.28 g, 102%). ^- MR (DMSO-D6) delta: 7.68 (1H, s), 7.41-7.39 (5H, m) , 6.96-6.94 (4H, m) , 5.22 (2H, s) , 5.21 (2H, s), 3.75 (6H, s), 3.53 (3H, s).

Reference： [1]Patent: WO2014/68388,2014,A1 .Location in patent: Paragraph 0448

6
[ 1609071-04-6 ]
[ 67496-78-0 ]
[ 1609070-77-0 ]

Yield	Reaction Conditions	Operation in experiment
95%		Compound X-5a (2.1 g, 5 mmol) was suspended into toluene (20 mL) , and thereto was then added <strong>[67496-78-0]quinuclidin-4-ylmethanamine</strong> (0.74 g, 5.3 mmol) at 0C. The mixture was stirred at 50C for 1 hour. Thereto was added acetic acid (0.57 mL, 10 mmol) . The resultant was stirred at reflux for 3 days. The reaction mixture was diluted with ethyl acetate and aqueous sodium hydroxide solution, then separated and washed with water and a saturated salt solution, and dried over magnesium sulfate . Magnesium sulfate was filtrated off, and then the liquid was concentrated under reduced pressure. The precipitated solid was then collected by filtration, and washed with diisopropyl ether to yield compound X-5 (2.6 g, 95%). 1H-NMR (CDC13) delta: 7.35 (4H, d, J = 8.7 Hz), 7.33 (2H, s), 6.90 (4H, d, J = 8.7 Hz), 5.18 (4H, s), 3.82 (6H, s), 3.38 (2H, br s), 2.85-2.81 (6H, m) , 1.42-1.38 (6H, m) .
95%		Compound X-5a (2.1 g, 5 mmol) was suspended in toluene (20 mL) Quinuclidin-4-ylmethanamine (0.74 g, 5.3 mmol) was then added thereto at 0 C. The mixture was stirred at 50 C. for 1 hour. Acetic acid (0.57 mL, 10 mmol) was added thereto.The obtained product was stirred under reflux for 3 days. The reaction mixture was diluted with ethyl acetate and aqueous sodium hydroxide solution then separated, washed with water and saturated salt solution and dried over magnesium sulfate. After filtering off the magnesium sulfate, the liquid was concentrated under reduced pressure. Next, the precipitated solid was collected by filtration, And washed with diisopropyl ether to give compound X-5 (2.6 g, 95%).

Reference： [1]Patent: WO2014/68388,2014,A1 .Location in patent: Paragraph 0201
[2]Patent: JP6377570,2018,B2 .Location in patent: Paragraph 0264; 0265

7
[ 1609072-26-5 ]
[ 1609071-04-6 ]
[ 1609072-27-6 ]

Yield	Reaction Conditions	Operation in experiment
37%	In ethanol; at 20℃;Reflux;	Compound 111d (1.50 g, 10.47 mmol) was dissolved in ethanol (50 mL), and then compound 110 a (4.40 g, 10.47 mmol) was added thereto. The mixture was stirred at room temperature for 1 day and then refluxed for 2 hours.The reaction mixture was evaporated. The liquid containing the compound was subjected to silica gel column chromatography, and the objective compound was eluted with ethyl acetate (3% triethylamine) / methanol. The target compound-containing fraction was concentrated under reduced pressure to give compound 111e (2.10 g, 37%).
	In ethanol; at 20℃; for 26h;Inert atmosphere; Reflux;	Compound llld (1.50 g, 10.47 mmol) was dissolved into ethanol (50 mL) , and thereto was then added compound 110a (4.40 g, 10.47 mmol) . The mixture was stirred at rt for 1 day, then reflux for 2 hour. The reaction mixture was evaporated. The compound-containing liquid was subjected to silica gel column chromatography to elute out the desired compound with ethyl acetate(3% triethylamine) /methanol

Reference： [1]Patent: JP6377570,2018,B2 .Location in patent: Paragraph 0602; 0605
[2]Patent: WO2014/68388,2014,A1 .Location in patent: Paragraph 0453

8
C₈H₁₇N₃*2ClH [ No CAS ]
[ 1609071-04-6 ]
C₃₂H₃₆N₄O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium acetate; In 1,4-dioxane; at 20℃; for 1h;Inert atmosphere;	A suspension of Compound 122e (17.6 g, 77 mmol) in 1, 4-dioxane (144 mL) was added sodium acetate (31.6 g, 385 mmol) and Compound 110a (38.8 g, 92 mmol). After stirring at room temperature for 1 hour, thereto was added acetic acid (22.02 ml, 385 mmol) . After stirring at room temperature for overnight, thereto was stirred at 70C for 1.5 hours. Then thereto was added 2 mol/L sodium hydroxide aqueous solution until it gave a pH of 12.0 at 0C, followed by extraction with ethyl acetate twice time . The combined organic layer was washed with saturated brine, and then was dried with anhydrous sodium sulfate. The inorganic substance was removed by filtration, and then concentrated under reduced pressure. Thereto was added 5% triethylamine and methanol solution in ethyl acetate to precipitate a solid. The solid was collected by filtration, so as to yield compound 122f as a white solid. Yielded amount: 30.96 g (72%) 1H-NMR (DMS0-D6) delta: 1.40 (6H, t, J = 7.47 Hz), 2.64 (6H, t, J = 7.47 Hz), 3.59.(2H, s) , 3.75 (6H, s), 5.11 (2H, s)", 5.12 (2H, s), 6.94 (4H, d, J= 8.28 Hz), 7.38 (4H, d, J = 8.28 Hz), 7.52 (2H, s) .

Reference： [1]Patent: WO2014/68388,2014,A1 .Location in patent: Paragraph 0480

9
[ 7154-73-6 ]
[ 1609071-04-6 ]
[ 1609071-05-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	In toluene; at 0 - 20℃; for 0.5h;Inert atmosphere;	Compound le (1.88 g, 4.5 mmol) was suspended into toluene (20 mL) , and thereto was then added aminoethylpyrrolidine (0.60 mL, 4.7 mmol) at 0C. The mixture was stirred at rt for 30 minutes. Thereto was added acetic acid (0.28 mL, 4.9 mmol) . The resultant mixture was stirred at reflux for 30 minutes . The reaction mixture was diluted with ethyl acetate and aqueous sodium hydroxide solution, then separated and washed with water and a saturated salt solution, and dried over magnesium sulfate. Magnesium sulfate was filtrated off, and then the liquid was concentrated under reduced pressure. The precipitated solid was then collected by filtration, and washed with diisopropyl ether to yield compound If (2.10 g, 91%) . 1H-NMR (CDC13) delta: 7.36-7.32 (6H, m) , 6.92-6.89 (4H, m) , 5.17 (4H, s), 3.81 (6H, s), 3.78-3.73 (2H, m) , 2.72-2.68 (2H, m) , 2.56 (4H, br s) , 1.74 (4H, br s) .
91%		Compound 1e (1.88 g, 4.5 mmol) was suspended in toluene (20 mL), and then aminoethyl pyrrolidine (0.60 mL, 4.7 mmol) was added thereto at 0 C. The mixture was stirred at room temperature for 30 minutes. acetic acid (0.28 mL, 4.9 mmol) was added thereto. The resulting mixture was stirred under reflux for 30 minutes. The reaction mixture was diluted with ethyl acetate and aqueous sodium hydroxide solution then separated, washed with water and saturated salt solution and dried over magnesium sulfate. After filtering off the magnesium sulfate, the liquid was concentrated under reduced pressure. Next, the precipitated solid was collected by filtration and washed with diisopropyl ether to give Compound 1f (2.10 g, 91%).

Reference： [1]Patent: WO2014/68388,2014,A1 .Location in patent: Paragraph 0229
[2]Patent: JP6377570,2018,B2 .Location in patent: Paragraph 0299; 0304

10
C₈H₁₅N₃ [ No CAS ]
[ 1609071-04-6 ]
[ 1609072-55-0 ]

Yield	Reaction Conditions	Operation in experiment
56%		A suspension of Compound 123b (6.97 g, 45.5 mmol) in dimethylformamide (70 mL) was added Compound llOf (20.08 g, 47.8 mmol) at 0C. After stirring at room temperature for 2 hours, thereto was added O-Benzotriazole-N, , 1 , ' -tetramethyluronium hexafluorophosphate (20.70 g, 54.6 mmol) at 0C. After stirring at room temperature for 4 hours, thereto was added acetic acid (26.0 ml, 455 mmol) and sodium cyanoborohydride (4.29 g, 68.2 mmol) at 0C. After stirring at room temperature for overnight, thereto was added 2 mol/L sodium hydroxide aqueous solution, followed by extraction with ethyl acetate twice time . The combined organic layer was washed with water and saturated brine, and then was dried with anhydrous sodium sulfate . The inorganic substance was removed by filtration, and then concentrated under reduced pressure. Thereto was added diisopropyl ether to precipitate a solid. The solid was collected by filtration, so as to yield compound 123c as a yellow solid. Yielded amount: 14.19 g, (56%) XH-N R (DMSO-D6) delta: 1.37 (6H, t, J= 7.59 Hz) , 2.65 (2H, d, J = 6.02 Hz), 2.73 (6H, t, J= 7.59 Hz), 3.75 (6H, s), 5.23 (4H, s), 6.95 (4H, d, J= 8.66 Hz), 7.37 (4H, d, J= 8.66 Hz), 7.46 (2H, s) .
56%		In dimethylformamide (70 mL)Compound 110a (20.08 g, 47.8 mmol) was added at 0 C. to a suspension of compound 123b (6.97 g, 45.5 mmol). After stirring at room temperature for 2 hours, O-benzotriazole-N, N, N ', N'-tetramethyluronium hexafluorophosphate (20.70 g, 54.6 mmol) was added thereto at 0 C. After stirring at room temperature for 4 hours, acetic acid (26.0 ml, 455 mmol) and sodium cyanoborohydride (4.29 g, 68.2 mmol) were added at 0 C. After stirring overnight at room temperature, a 2 mol / L sodium hydroxide aqueous solution was added thereto, followed by extraction twice with ethyl acetate. The combined organic layers were washed with water and saturated brine and then dried over anhydrous sodium sulfate. The inorganic substance was filtered off and then concentrated under reduced pressure. To this was added diisopropyl ether to precipitate a solid. The solid was collected by filtration, whereby Compound 123c was obtained as a yellow solid.Yield: 14.19 g, (56%)

Reference： [1]Patent: WO2014/68388,2014,A1 .Location in patent: Paragraph 0484
[2]Patent: JP6377570,2018,B2 .Location in patent: Paragraph 0646; 0649

11
[ 531-88-4 ]
[ 1609071-04-6 ]