[ CAS No. 902586-59-8 ] {[proInfo.proName]}

Name: 902586-59-8|9-Chloro-5,6,7,8-tetrahydroacridine-3-carboxylic acid|95%
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Quality Control of [ 902586-59-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 902586-59-8 ]

CAS No. :	902586-59-8	MDL No. :	MFCD14779907
Formula :	C₁₄H₁₂ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WBIKDLIOIPPDKH-UHFFFAOYSA-N
M.W :	261.70	Pubchem ID :	4340614
Synonyms :

Safety of [ 902586-59-8 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 902586-59-8 ]

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

Downstream synthetic route of [ 902586-59-8 ]

[ 902586-59-8 ] Synthesis Path-Downstream 1~19

1
[ 1314749-35-3 ]
[ 902586-59-8 ]

Yield	Reaction Conditions	Operation in experiment
88%		A suspension of 9-oxo-5,6,7,8,9,10-hexahydro-acridine-3-carboxylic acid (VIa) (10 g, 4.1 mmols) in phosphorous oxychloride (50 mL) was heated to 100 C. for 1 h. Reaction completion was monitored by TLC. After completion, the reaction mixture was cooled to 25 C. and excess phosphorous oxychloride was removed under vacuum. The residue was mixed with ice (50 g) and the pH was adjusted to 4-5 with solid sodium bicarbonate. The solid obtained was filtered, washed with water (250 mL) and dried under vacuum to get 9.6 g (88%) of compound (Vila) as a white solid.1H NMR (300 MHz, DMSO) δ 13.37 (s, 1H), 8.44 (s, 1H), 8.19-8.16 (d, 1H, J=8.7 Hz), 8.09-8.07 (dd, 1H, J=8.7 Hz, 1.5 Hz), 3.06 (m, 2H), 2.96 (m, 2H), 1.99-1.89 (m, 4H).MS: calcd for C14H12ClNO2, 261.06. found 261.8 (M+H)+.
88%	With trichlorophosphate; at 100℃; for 1h;	Step 2: halogenation; 9-chloro-5,6,7,8-tetrahydroacridine-3-carboxylic acid (VIIa); A suspension of 9-oxo-5, 6, 7, 8, 9, 10-hexahydro-acridine-3-carboxylic acid (VIa) (10 g, 4.1 mmols) in phosphorous oxychloride (50 mL) was heated to 100C for 1 h. Reaction completion was monitored by TLC. After completion, the reaction mixture was cooled to 25C and excess phosphorous oxychloride was removed under vacuum. The residue was mixed with ice (50 g) and the pH was adjusted to 4-5 with solid sodium bicarbonate. The solid obtained was filtered, washed with water (250 mL) and dried under vacuum to get 9.6 g (88%) of compound (VIIa) as a white solid. 1H NMR (300 MHz, DMSO) δ 13.37 (s, 1H), 8.44 (s, 1H), 8.19-8.16 (d, 1H, J = 8.7 Hz), 8.09-8.07 (dd, 1H, J = 8.7 Hz, 1.5 Hz), 3.06 (m, 2H), 2.96 (m, 2H), 1.99-1.89 (m, 4H). MS: calcd for C14H12ClNO2, 261.06; found 261.8 (M+H)+.

Reference： [1]Patent: US2011/177105,2011,A1 .Location in patent: Page/Page column 9
[2]Patent: EP2357176,2011,A1 .Location in patent: Page/Page column 14

2
[ 10312-55-7 ]
[ 902586-59-8 ]

Reference： [1]Patent: US2011/177105,2011,A1

3
[ 902586-59-8 ]
[ 838814-74-7 ]
[ 902438-68-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In N,N-dimethyl-formamide; at 20℃;	To a 0.1M DMF solution of the heterocyclic acids VII, triethylamine was added (2 equiv.) followed by the corresponding amines (1 equiv.) and coupling agent (TBTU, HATU, OHBT, 1 equiv.). The corresponding mixtures were stirred for 1-12 h at 20 C. Concentrated HCl was added and after 5 min stirring, the mixtures were under vacuum. The crude compounds were extracted with 20 mL d'AcOEt, washed with 10 mL of aqueous 0.5M NaHCO3 solution and 10 mL of water. The organics phase were dried over MgSO4 then evaporated under vacuum. Purification using silicagel (gradient CH2Cl2 CH2Cl2/MeOH 9/1) or preparative LC/MS affords the pure corresponding amides.Selected data of some of the compounds that were prepared by application or adaptation of the method disclosed above are shown below:9-Chloro-5,6,7,8-tetrahydro-acridine-3-carboxylic acid [1-(3-methyl-benzyl)-piperidin-4-ylmethyl]-amide (1)1H NMR (400 MHz, DMSO-d6) δ 8.77 (t, J=5.7 Hz, 1H), 8.47 (d, J=1.8 Hz, 1H), 8.17 (d, J=8.8 Hz, 1H), 8.04 (dd, J=1.7, 8.7 Hz, 1H), 7.36 (s, 1H), 7.18 (t, J=7.5 Hz, 1H), 7.09 (s, 1H), 7.07 (d, J=7.7 Hz, 1H), 7.04 (d, J=7.5 Hz, 1H), 3.38 (s, 2H), 3.32-3.29 (m, 2H), 3.21 (d, J=6.7 Hz, 2H), 3.06 (m, 2H), 2.98 (m, 2H), 2.79 (m, 2H), 2.28 (s, 3H), 1.94-1.84 (m, 6H), 1.69 (s, 1H), 1.66 (s, 1H), 1.63-1.53 (m, 1H), 1.28-1.14 (m, 2H).MS: calcd for C28H32ClN3O, 461.22. found 462.17 (M+H)+.
	With triethylamine; In N,N-dimethyl-formamide; at 20℃;	Step 3 : Amide formation; To a 0.1M DMF solution of the heterocyclic acids VII, triethylamine was added (2 equiv.) followed by the corresponding amines (1 equiv.) and coupling agent (TBTU, HATU, OHBT, 1 equiv.). The corresponding mixtures were stirred for 1-12 h at 20C. Concentrated HCl was added and after 5 min stirring, the mixtures were under vacuum. The crude compounds were extracted with 20 mL d'AcOEt, washed with 10 mL of aqueous 0.5M NaHCO3 solution and 10 mL of water. The organics phase were dried over MgSO4 then evaporated under vacuum. Purification using silicagel (gradient CH2Cl2 CH2Cl2/MeOH 9/1) or preparative LC/MS affords the pure corresponding amides. Selected data of some of the compounds that were prepared by application or adaptation of the method disclosed above are shown below:9-Chloro-5,6,7,8-tetrahydro-acridine-3-carboxylic acid [1-(3-methyl-benzyl)-piperidin-4-ylmethyl]-amide (1) 1H NMR (400 MHz, DMSO-d6) δ 8.77 (t, J = 5.7 Hz, 1H), 8.47 (d, J = 1.8 Hz, 1H), 8.17 (d, J = 8.8 Hz, 1H), 8.04 (dd, J = 1.7, 8.7 Hz, 1H), 7.36 (s, 1H), 7.18 (t, J = 7.5 Hz, 1H), 7.09 (s, 1H), 7.07 (d, J = 7.7 Hz, 1H), 7.04 (d, J = 7.5 Hz, 1H), 3.38 (s, 2H), 3.32-3.29 (m, 2H), 3.21 (d, J = 6.7 Hz, 2H), 3.06 (m, 2H), 2.98 (m, 2H), 2.79 (m, 2H), 2.28 (s, 3H), 1.94-1.84 (m, 6H), 1.69 (s, 1H), 1.66 (s, 1H), 1.63-1.53 (m, 1H), 1.28-1.14 (m, 2H). MS: calcd for C28H32ClN3O, 461.22; found 462.17 (M+H)+.

Reference： [1]Patent: US2011/177105,2011,A1 .Location in patent: Page/Page column 9; 10
[2]Patent: EP2357176,2011,A1 .Location in patent: Page/Page column 14

4
[ 902586-59-8 ]
piperazine-1-carboxylic acid propyl ester [ No CAS ]
propyl 4-(9-chloro-5,6,7,8-tetrahydroacridine-3-carbonyl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; HATU; In N,N-dimethyl-formamide; at 0℃;	General procedure: Step 3: General Procedure C Condition 1: Amide coupling using l-[bis(dimethylamino)methylene]-lH-l,2,3-triazolo[4,5- b]pyridinium 3-oxid hexafluorophosphate (HATU) Chlorinated compound S2 (1 equiv), amine (VI) (1-2 equiv) and triethylamine (2-4 equiv) were dissolved in N,N-dimethylformamide (0.1 M) and the solution was cooled to 0 C. HATU (1.5 equiv) was added and the reaction was quenched upon completion based on LCMS analysis (<1 h) by the addition of water. The aqueous layer was extracted 3-5 times with ethyl acetate, and the combined organic layers were washed with saturated sodium bicarbonate, brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography to afford compound with general formula (IV). Propyl 4-(9-chloro-5,6,7,8-tetrahydroacridine-3-carbon l)piperazine-l-carboxylate (A001) Compound A001 was prepared according to General Procedure CI, using commercially available 9- chloro-5,6,7,8-tetrahydroacridine-3-carboxylic acid and n-propyl piperazine- 1-carboxylate as starting materials. *H NMR (400 MHz, CDC13) δ 8.19 (d, / = 8.6 Hz, 1 H), 7.94 (d, / = 1.2 Hz, 1 H), 7.65 (dd, / = 8.6, 1.5 Hz, 1 H), 3.97 (t, / = 6.6 Hz, 2 H), 3.80-3.28 (m, 8 H), 3.06 (s, 2 H), 2.99 (s, 2 H), 1.90 (s, 4 H), 1.66-1.47 (m, 2 H), 0.89 (t, / = 7.3 Hz, 3 H). LCMS (ESI-TOF) m/z 416.1 [M + H+] with a purity of >95%.

Reference： [1]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 978 - 984
[2]Patent: WO2017/61957,2017,A1 .Location in patent: Page/Page column 75; 119

5
[ 902586-59-8 ]
C₁₀H₁₁ClN₂O₂ [ No CAS ]
9-chloro-N-(5-chloro-2,4-dimethoxyphenyl)-N-(cyanomethyl)-5,6,7,8-tetrahydroacridine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		9-Chloro-5,6,7,8-tetrahydroacridine-3-carboxylic acid (100 mg, 0.38 mmol) was dissolved in 2 ml of N,N-dimethylformamide (DMF) and charged with 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (144 mg, 0.38 mmol). After stirring at room temperature for 30 min, the mixture was then charged with 3-((5-chloro-2,4-dimethoxyphenyl)amino)propanenitrile (91 mg, 0.38 mmol). The resulting solution was stirred at 110 C for 1 h, dilutedwith of 50 ml of ethyl acetate, and then extracted with ethyl acetate (2 × 100 ml).The combined organic layers were washed with brine (3 × 200 ml), dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified on a silica gel column eluting with ethyl acetate/petroleum ether (1:100 to 1:10) to afford the title compound (110 mg, 0.30 mmol, 78% yield) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.01 (d, J = 8.7 Hz, 1H), 7.82 (d, J = 1.7 Hz, 1H), 7.62-7.59 (m, 2H), 6.67 (s, 1H), 4.90-4.72 (m, 2H), 3.79 (s, 3H), 3.73 (s, 3H),2.98-2.90 (m, 4H), 1.85 (m, 4H). 13C NMR (150 MHz, DMSO-d6) δ 21.8, 21.8, 27.0, 33.5, 37.4, 56.4, 56.4, 98.1, 111.7, 116.3, 122.7, 123.0, 125.1, 125.8, 127.8,129.7, 130.3, 135.6, 139.8, 144.8, 154.5, 155.3, 160.6, 170.0. HRMS m/z 470.1033 (M + H+, C24H22O3N3Cl2, requires 470.1029).

Reference： [1]Nature,2017,vol. 550,p. 534 - 538

6
[ 902586-59-8 ]
C₁₃H₁₈ClNO₃ [ No CAS ]
9-chloro-N-(5-chloro-2,4-dimethoxyphenyl)-N-((3-methyloxetan-3-yl)methyl)-5,6,7,8-tetrahydroacridine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: 9-Chloro-5,6,7,8-tetrahydroacridine-3-carboxylic acid (100 mg, 0.38 mmol) was dissolved in 2 ml of N,N-dimethylformamide (DMF) and charged with 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (144 mg, 0.38 mmol). After stirring at room temperature for 30 min, the mixture was then charged with 3-((5-chloro-2,4-dimethoxyphenyl)amino)propanenitrile (91 mg, 0.38 mmol). The resulting solution was stirred at 110 C for 1 h, dilutedwith of 50 ml of ethyl acetate, and then extracted with ethyl acetate (2 × 100 ml).The combined organic layers were washed with brine (3 × 200 ml), dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified on a silica gel column eluting with ethyl acetate/petroleum ether (1:100 to 1:10) to afford the title compound (110 mg, 0.30 mmol, 78% yield) of the title compound.

Reference： [1]Nature,2017,vol. 550,p. 534 - 538

7
[ 902586-59-8 ]
C₁₁H₁₆ClNO₄ [ No CAS ]
9-chloro-N-(5-chloro-2,4-dimethoxyphenyl)-N-(2,3-dihydroxypropyl)-5,6,7,8-tetrahydroacridine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: 9-Chloro-5,6,7,8-tetrahydroacridine-3-carboxylic acid (100 mg, 0.38 mmol) was dissolved in 2 ml of N,N-dimethylformamide (DMF) and charged with 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (144 mg, 0.38 mmol). After stirring at room temperature for 30 min, the mixture was then charged with 3-((5-chloro-2,4-dimethoxyphenyl)amino)propanenitrile (91 mg, 0.38 mmol). The resulting solution was stirred at 110 C for 1 h, dilutedwith of 50 ml of ethyl acetate, and then extracted with ethyl acetate (2 × 100 ml).The combined organic layers were washed with brine (3 × 200 ml), dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified on a silica gel column eluting with ethyl acetate/petroleum ether (1:100 to 1:10) to afford the title compound (110 mg, 0.30 mmol, 78% yield) of the title compound.

Reference： [1]Nature,2017,vol. 550,p. 534 - 538

8
[ 109-83-1 ]
[ 902586-59-8 ]
9-chloro-N-(2-hydroxyethyl)-N-methyl-5,6,7,8-tetrahydroacridine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: 9-Chloro-5,6,7,8-tetrahydroacridine-3-carboxylic acid (100 mg, 0.38 mmol) was dissolved in 2 ml of N,N-dimethylformamide (DMF) and charged with 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (144 mg, 0.38 mmol). After stirring at room temperature for 30 min, the mixture was then charged with 3-((5-chloro-2,4-dimethoxyphenyl)amino)propanenitrile (91 mg, 0.38 mmol). The resulting solution was stirred at 110 C for 1 h, dilutedwith of 50 ml of ethyl acetate, and then extracted with ethyl acetate (2 × 100 ml).The combined organic layers were washed with brine (3 × 200 ml), dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified on a silica gel column eluting with ethyl acetate/petroleum ether (1:100 to 1:10) to afford the title compound (110 mg, 0.30 mmol, 78% yield) of the title compound.

Reference： [1]Nature,2017,vol. 550,p. 534 - 538

9
[ 902586-59-8 ]
[ 41458-73-5 ]
9-chloro-N-methyl-N-(2-morpholino-2-oxo-ethyl)-5,6,7,8-tetrahydroacridine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: 9-Chloro-5,6,7,8-tetrahydroacridine-3-carboxylic acid (100 mg, 0.38 mmol) was dissolved in 2 ml of N,N-dimethylformamide (DMF) and charged with 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (144 mg, 0.38 mmol). After stirring at room temperature for 30 min, the mixture was then charged with 3-((5-chloro-2,4-dimethoxyphenyl)amino)propanenitrile (91 mg, 0.38 mmol). The resulting solution was stirred at 110 C for 1 h, dilutedwith of 50 ml of ethyl acetate, and then extracted with ethyl acetate (2 × 100 ml).The combined organic layers were washed with brine (3 × 200 ml), dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified on a silica gel column eluting with ethyl acetate/petroleum ether (1:100 to 1:10) to afford the title compound (110 mg, 0.30 mmol, 78% yield) of the title compound.

Reference： [1]Nature,2017,vol. 550,p. 534 - 538

10
[ 120-43-4 ]
[ 902586-59-8 ]
ethyl 4-(9-chloro-5,6,7,8-tetrahydroacridine-3-carbonyl)piperazine-1-carboxylate [ No CAS ]