[ CAS No. 720689-55-4 ] {[proInfo.proName]}

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Quality Control of [ 720689-55-4 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 720689-55-4 ]

CAS No. :	720689-55-4	MDL No. :	MFCD16987636
Formula :	C₁₄H₁₉NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	217.31	Pubchem ID :	-
Synonyms :

Safety of [ 720689-55-4 ]

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Application In Synthesis of [ 720689-55-4 ]

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

Downstream synthetic route of [ 720689-55-4 ]

[ 720689-55-4 ] Synthesis Path-Downstream 1~9

1
[ 720689-55-4 ]
[ 32383-03-2 ]
dimethyl 6-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-2,3-pyridinecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate In DMF (N,N-dimethyl-formamide) at 80℃; for 3h;	231 A mixture of 3-cyclobutyl-2, 3,4, 5-tetrahydro-1 H-benzo [d] azepin-7-ol (E3) (1. 5g), dimethyl 6- chloro-2, 3-pyridinedicarboxylate (1.58g ; Kenji Niiyama et al. Bioorg. Med. Chem Lett. 12, 21,2002, 3041-3054) and cesium carbonate (4.4g) in dry DMF (30ml) was heated at 80 °C for 3h. The cooled mixture was partitioned between water (20ML) and ethyl acetate (3X100ML), the combined organic extracts were washed with brine (2X100ML) and dried (Na 2SO4). The solvent was evaporated to give an oil which was purified by column chromatography eluting with a mixture of. 880 ammonia: methanol : dichloromethane (0.5 : 4.5 : 95) to afford the title compound (E231); MS (ES+) m/e 411 [M+H] +.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2004/56369, 2004, A1 Location in patent: Page/Page column 71

2
[ 13195-50-1 ]
[ 720689-55-4 ]
3-cyclobutyl-7-[(5-nitro-2-thienyl)oxy]-2,3,4,5-tetrahydro-1H-3-benzazepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 80℃; for 16h;	A mixture of <strong>[13195-50-1]2-bromo-5-nitrothiophene</strong> (478 mg, 2.3 MMOL), 3-cyclobutyl-2, 3,4, 5-tetrahydro- 1 H-BENZO [d] azepin-7-ol (E3) (500 mg, 2.3 MMOL) and potassium carbonate (765 mg, 5.5 mmol) in dimethylformamide (10 ml) was stirred at 80 °C for 16 hours. The reaction mixture was cooled, diluted with ethyl acetate and washed with water, brine and dried (sodium sulfate). CONCENTRATION IN VACUO and purification of the resulting residue by column chromatography. 880 ammonia: methanol : DICHLOROMETHANE (1: 8: 300) afforded the title compound (E211) ; MS (ES+) m/e 345 [M+H] +.

Reference： [1]Patent: WO2004/56369,2004,A1 .Location in patent: Page/Page column 65

3
[ 720689-55-4 ]
[ 54189-82-1 ]
[ 720690-73-3 ]

Yield	Reaction Conditions	Operation in experiment
66%		NaH (60% dispersion in mineral oil, 27.6 mg, 0.69 mmol) was added with stirring to a solution of compound 6 (100 mg, 0.46 mmol) in DMSO (3 mL) portionwise. The mixture was stirred for 30 min and compound 7 (156 mg, 0.92 mmol) was added. After the reaction mixture was heated and stirred at 120 C overnight, it was cooled and poured into ice-water, extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified with preparative TLC plate (200:14:1 CH2Cl2/MeOH/NH4OH) to afford 9 (107 mg, 66%) as a white solid
		Sodium hydride (60% disp. in mineral oil, 60 mg, 1.5 MMOL) was added to a stirred solution of 3-cyclobutyl-2, 3, 4, 5-TETRAHYDRO-1 H-BENZO [D] AZEPIN-7-OL (E3) (200 mg, 0.9 MMOL) in dimethyl sulfoxide (10 ml). After 0.5 hours, 6-CHLORO-N-METHYL-NICOTINAMIDE (D10) (400 mg, 2.5 MMOL) was added and the reaction mixture was heated to 120 C for 6 hours. The reaction was allowed to cool and the crude mixture was applied to a SCX ion exchange cartridge (Varian bond-elute, 10 g) and washed with methanol and then a mixture of. 880 ammonia: methanol (1: 9). The combined basic fractions were reduced in vacuo to afford the title compound (E121). 1H NMR (DMSO-D6) 88. 56 (1H, dd, J = 2. 4,0. 4Hz), 8.48 (1H, BR M), 8.20 (1 H, dd, J = 8. 4,2. 4 HZ), 7.16 (1 H, d, J = 8. 0 Hz), 7.03 (1H, dd, J = 8. 4,0. 4 HZ), 6.91 (1 H, D, J = 2.4Hz), 6.86 (1H, dd, J = 8.0, 2. 4HZ), 2.87-2. 77 (8H, m), 2.36 (4H, m), 2.00 (2H, m), 1.78 (2H, m), 1.58 (2H, m); MS (ES+) m/e 352 [M+H] +
		Sodium hydride (0. 331G, 8.28 MMOL, 60% disp. in mineral oil) was added to a stirred solution of 3-cyclobutyl-2, 3, 4, 5-TETRAHYDRO-1H-BENZO [d] azepin-7-ol (E3) (1.5g, 6.9 MMOL) IN dimethyl sulfoxide (15 ML). After 0.5 hours, 6-chloro-N-methyl-nicotinamide (D10) (2.34g, 13.8 MMOL) was added and the reaction mixture was heated to 100 C for 18 hours. The reaction was allowed to cool to room temperature and then partitioned between ethyl acetate and water. The ethyl acetate layer was separated and the water layer washed with further volumes of ethyl acetate. The combined organic layers were then washed with water, brine, dried (NA2SO4) and then filtered. The mixture was concentrated IN VACUO and the resulting residue was purified by column chromatography eluting with a mixture of. 880 ammonia: ethanol : dichloromethane (0.5 : 4.5 : 95 then 1: 9: 90) to afford the title compound (E121) which then was recrystallised from toluene.'H NMR (DMSO-d6) 8 8.56 (1H, dd, J = 2.4, 0.4Hz), 8.48 (1H, br m), 8.20 (1H, dd, J = 8.4, 2.4 Hz), 7.16 (1H, d, J = 8.0 Hz), 7.03 (1H, dd, J = 8. 4,0. 4 HZ), 6.91 (1H, d, J = 2. 4HZ), 6.86 (1H, dd, J = 8. 0,2. 4Hz), 2.87-2. 77 (8H, m), 2.36 (4H, m), 2.00 (2H, m), 1.78 (2H, m), 1.58 (2H, m); MS (ES+) m/e 352 [M+H] +.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4713 - 4718
[2]Patent: WO2004/56369,2004,A1 .Location in patent: Page/Page column 46-47
[3]Patent: WO2004/56369,2004,A1 .Location in patent: Page/Page column 47

4
[ 720689-55-4 ]
[ 57356-64-6 ]
3-cyclobutyl-7-[2-(1-piperidinyl)-5-pyrimidinyl]oxy}-2,3,4,5-tetrahydro-1H-3-benzazepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol With pyridine; sodium hydride; copper(I) bromide at 0 - 20℃; for 0.5h; Stage #2: 5-bromo-2-(piperidin-1-yl)pyrimidine for 2h; Heating / reflux;	140 Sodium hydride (60% disp. in mineral oil, 44 mg, 1.1 MMOL) was added to a stirred solution of 3-cyclobutyl-2, 3,4, 5-tetrahydro-1H-benzo [d] azepin-7-ol (E3) (200 mg, 0.92 MMOL) and copper (I) bromide (184 mg, 1.3 MMOL) in pyridine (10 ml) at 0 °C. After stirring for 0.5 hour at room temperature, 5-BROMO-2-(1-PIPERIDINYL) pyrimidine (D32) (0. 669 G, 2.8 MMOL) was added and the reaction mixture heated at reflux for 2 hours. The reaction was allowed to cool, filtered and the filtrate was concentrated in vacuo. The crude residue was dissolved with ethyl acetate and washed with water and brine. The organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Purification of the resulting residue by column chromatography eluting with a mixture of. 880 ammonia: ethanol : DICHLOROMETHANE (0.25 : 2.25 : 97.5 to 1: 9: 90) afforded the title compound (E140). MS (ES+) m/e 379 [M+H] +.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2004/56369, 2004, A1 Location in patent: Page/Page column 51-52

5
[ 720689-55-4 ]
[ 38275-57-9 ]
5-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-2-pyrimidinecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		3-Cyclobutyl-2, 3,4, 5-TETRAHYDRO-1H-3-BENZAZEPIN-7-OL (E3) (1.81 g, 8.33 MMOL) was dissolved in pyridine (40 ml) and sodium hydride (60% in mineral oil, 0.40 g, 10.0 MMOL) was added with stirring under argon at 0 C. The mixture was left to stir for 5 minutes. Copper (I) bromide (1.68 g, 11.7 MMOL) was added and the mixture allowed to warm to room temperature over 30 minutes. 5-Bromo-2-pyrimidinecarbonitrile (D38) (2.30 g, 12.5 MMOL) in pyridine (8 ml) was added and the mixture heated at 100 C for 1 hour. The mixture was allowed to cool to room temperature and the solvent removed in vacuo. The crude product was purified by column chromatography, eluting with a mixture of 0.880 ammonia: methanol : dichloromethane (0.2 : 1.8 : 98) to afford the title compound (E177A) ; MS (ES+) m/e 321 [M+H] +.

Reference： [1]Patent: WO2004/56369,2004,A1 .Location in patent: Page/Page column 58

6
[ 19745-07-4 ]
[ 720689-55-4 ]
7-[(5-chloro-2-pyrazinyl)oxy]-3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		3-CYCLOBUTYL-2, 3,4, 5-TETRAHYDRO-1H-BENZO [d] azepin-7-ol (E3) (184 mg, 0.85 MMOL) was dissolved in dry dimethylformamide (3 ml), cooled to 0 °C and treated with sodium hydride (60 percent in mineral oil, 36 mg, 0.89 MMOL). The mixture was allowed to warm to room temperature over 30 minutes. A solution of 2, 5-dichloropyrazine (D47) (139 mg, 0.94 MMOL) in dry dimethylformamide (1 ml) was added and the mixture stirred at room temperature for 5 hours. The mixture was applied to a SCX column and washed with methanol then a mixture of. 880 ammonia/methanol (1: 9). The basic fractions were combined and concentrated in vacuo to afford the title compound (268 mg); MS (ES+) m/e 330 [M+H] +.

Reference： [1]Patent: WO2004/56369,2004,A1 .Location in patent: Page/Page column 78

7
[ 720689-55-4 ]
[ 3034-48-8 ]
3-cyclobutyl-7-[(5-nitro-1,3-thiazol-2-yl)oxy]-2,3,4,5-tetrahydro-1H-3-benzazepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Sodium hydride (60percent disp. in mineral oil, 150 mg, 3.66 MMOL) was added to a stirred solution of 3-cyclobutyl-2, 3,4, 5-TETRAHYDRO-1H-BENZO [d] azepin-7-ol (E3) (530 mg, 2.43 MMOL) in dimethylformamide (10 ML) at 5 °C. After 0.5 hours a solution of 2-bromo-5-nitro- 1, 3-thiazole (1.0 g, 4.78 MMOL) in dimethylformamide (5 ML) was added and the reaction mixture was allowed to warm to room temperature and stir for 2 hours. The reaction mixture was diluted with ethyl acetate and the organic layer was washed with water, brine, dried (sodium sulfate) and concentrated in vacuo. Purification by column chromatography eluting with a mixture of 0.880 ammonia: methanol : DICHLOROMETHANE (0.25 : 2.25 : 97.5) afforded the title compound (E210A) ; MS (ES+) m/e 346 [M+H] +.

Reference： [1]Patent: WO2004/56369,2004,A1 .Location in patent: Page/Page column 64

8
[ 6271-78-9 ]
[ 720689-55-4 ]
6-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]pyridine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%		NaH (60% dispersion in mineral oil, 55.2 mg, 1.38 mmol) was added with stirring to a solution of compound 6 (200 mg, 0.92 mmol) in DMSO (6 mL) portionwise. The mixture was stirred for 30 min and <strong>[6271-78-9]6-chloronicotinamide</strong> (288 mg, 1.84 mmol) was added. After the reaction mixture was heated and stirred at 120 C overnight, it was cooled and poured into ice-water, extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified with preparative TLC plate (200:16:1 CH2Cl2/MeOH/NH4OH) to afford 8 (229 mg, 71%) as a white solid,

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4713 - 4718

9
[ 37682-06-7 ]
[ 720689-55-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: borane-THF / tetrahydrofuran / 0 °C / Reflux 2.1: acetic acid / dichloromethane / 0.5 h / 0 - 20 °C 2.2: 20 °C 3.1: hydrogen bromide; tetra-(n-butyl)ammonium iodide / acetic acid / 100 °C

Reference： [1]Wang, Min; Gao, Mingzhang; Steele, Brandon L.; Glick-Wilson, Barbara E.; Brown-Proctor, Clive; Shekhar, Anantha; Hutchins, Gary D.; Zheng, Qi-Huang [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 14, p. 4713 - 4718]

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[ CAS No. 720689-55-4 ] {[proInfo.proName]}

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[ 720689-55-4 ] Synthesis Path-Downstream 1~9

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