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[ CAS No. 612532-52-2 ]

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2D3D

Chemical Structure| 612532-52-2

Chemical Structure| 612532-52-2

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Quality Control of [ 612532-52-2 ]

COA GC NMR CNMR HPLC/UPLC LC-MS

Related Doc. of [ 612532-52-2 ]

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Product Details of [ 612532-52-2 ]

CAS No. :	612532-52-2	MDL No. :	MFCD03412718
Formula :	C₉H₁₂FNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	169.20	Pubchem ID :	22115252
Synonyms :

Computed Properties of [ 612532-52-2 ]

TPSA :Topological Polar Surface Area	46.2	H-Bond Acceptor Count :	3
XLogP3 :	0.6	H-Bond Donor Count :	2
SP3 :	0.33	Rotatable Bond Count :	3

Safety of [ 612532-52-2 ]

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 [ 612532-52-2 ]

Upstream synthesis route of [ 612532-52-2 ]
Downstream synthetic route of [ 612532-52-2 ]

[ 612532-52-2 ] Synthesis Path-Upstream 1~2

1
[ 325-89-3 ]
[ 612532-52-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 16, p. 3685 - 3690
[2] Patent: US2006/183800, 2006, A1. Location in patent: Page/Page column 67-68

2
[ 459-57-4 ]
[ 612532-52-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 16, p. 3685 - 3690

[ 612532-52-2 ] Synthesis Path-Downstream 1~6

1
[ 612532-52-2 ]
4-oxo-6-(quinolin-7-yl)-4,5-dihydropyrazolo[1,5-a]pyrazine-2-carboxylic acid [ No CAS ]
N-[1-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-6-(7-quinolyl)-5H-pyrazolo[1,5-a]pyrazine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1%		Oxalyl chloride (280 pi, 3.3 mmol) was added to a suspension of 4-oxo-6-(quinolin-7-yl)-4,5-dihydropyrazolo[1,5-a]pyrazine-2-carboxylic acid (Intermediate 117A, 200 mg, 653 pmol) in di- chloromethane (5.5 ml), followed by one drop of DMF. After stirring at RT for 1H, the volatiles were removed under reduced pressure, and the residue was slowly added to a solution of <strong>[612532-52-2]3-amino-3-(4-fluorophenyl)propan-1-ol</strong> (110 mg, 653 pmol) and N,N-diisopropylethylamine (340 pi, 2.0 mmol) in dichloromethane (5.0 ml). The mixture was stirred at RT overnight. dichloro- methane and water were added, the layers were separated, and the aqueous layer was extract- ed with dichloromethane. The combined organic layers were dried over magnesium sulfate, fil- tered and concentrated. The residue was purified by preparative HPLC (Method P9) to afford the title compound. Yield: 2.1 mg (1% of theory). LC/MS [Method 7]: Rt = 0.70 min; MS (ESIpos): m/z = 458 [M+H]+. 1H-NMR (500 MHz, DMSO-d6): d [ppm] = 11.63 (br. s, 1H), 8.99 (dd, 1H), 8.91 (d, 1H), 8.45 (d, 1H), 8.43 (dd, 1H), 8.25 (s, 1H), 8.11 (d, 1H), 7.99 (dd, 1H), 7.61 (dd, 1H), 7.48-7.42 (m, 2H), 7.39 (d, 1H), 7.19-7.13 (m, 2H), 5.23-5.17 (m, 1H), 4.63 (t, 1H), 3.49-3.37 (m, 2H), 2.12-2.04 (m, 1H), 1.98-1.89 (m, 1H).

Reference： [1]Patent: WO2019/219517,2019,A1.Location in patent: Page/Page column 366-367

2
[ 612532-52-2 ]
[ 890147-33-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide; In water; for 18.0h;Heating / reflux;	Preparation of 3-amino-3-(4-fluorophenyl)-1-propanesulfonic acid; A solution of borane:tetrahydrofurane complex (1M, 100 mL) was added dropwise over 1 hour to a cold (0 C.) suspension of DL-3-amino-3-(4-fluorophenyl)propionoc acid (7.30 g, 39.9 mmol) in THF (40 mL). The mixture was heated to reflux for 22 hours. The mixture was then cooled to 0 C. and methanol (35 mL) was added over 15 minutes. The mixture was then heated to reflux for 30 minutes and concentrated to a thick oil. The oil was coevaporated 3 times with methanol (50 mL). The crude product was used directly in next step. The oil that was obtained in the previous step was dissolved in water and added dropwise to concentrated HBr (44 mL) The solution was heated at reflux for 18 hours. It was then concentrated to dryness (11.58 g). The solid was suspended in hot heptane/2-butanone then cooled to room temperature. Ether was added and the mixture was stirred for 30 minutes. The solid was collected by filtration and rinsed with ether (9.97 g, about 66% for two steps). The 3-bromo-1-(4-fluorophenyl)-1-propylamine hydrobromide (obtained in step 2, 32 mmol) was added to a solution of sodium sulfite (3.78 g, 30 mmol) in water (40 mL). The mixture was heated at 90 C. for 2.5 hours, and was then concentrated to a thick paste. Concentrated HCl (8 mL) was added to the paste. The resulting suspension was stirred for 20 minutes at room temperature. The solid was collected by filtration and rinsed with concentrated HCl (3×30 mL). The filtrated solid was concentrated to dryness. The solid was washed in ethanol/toluene then dried in vacuo (3.79 g). The solid was recrystallized in ethanol (25 mL) and water (6 mL). After cooling to room temperature, the solid was collected by filtration, rinsed with ethanol (2×5 mL) and dried overnight at 60 C. in a vacuum oven. The title compounds was obtained as a fine white crystalline solid, yield 2.37 g, 26% overall yield. 1H NMR 1H (500 MHz, D2O) delta 2.22-2.36 (m, 2H), 2.54-2.60 (m, 1H), 2.65-2.71(m, 1H), 4.37-4.40 (m, 1H), 7.07 (t, J=8.5 Hz, 2H), 7.26-7.31 (dd, J=8.3, 5.4 Hz, 2H); 13C (125 MHz, D2O) delta 28.82, 47.1, 53.5, 116.4 (d, J=22 Hz, 2C), 139.7 (d, J=11.6 Hz, 2C), 130.9, 163.2 (d, J=246 Hz, 2C); 19F (282 MHz, D2O) -112.9 to -113.0 (m); ES-MS 232 (M-1).

Reference： [1]Patent: US2006/183800,2006,A1.Location in patent: Page/Page column 67-68

3
[ 459-57-4 ]
[ 612532-52-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3685 - 3690

4
[ 612532-52-2 ]
[3-[3-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-2,4,6-trioxo-[1,3,5]triazinan-1-yl]-1-(4-fluoro-phenyl)-propyl]-carbamic acid <i>tert</i>-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3685 - 3690

5
[ 612532-52-2 ]
1-[3-amino-3-(4-fluoro-phenyl)-propyl]-3-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-[1,3,5]triazinane-2,4,6-trione [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3685 - 3690

6
[ 325-89-3 ]
[ 612532-52-2 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation of 3-amino-3-(4-fluorophenyl)-1-propanesulfonic acid A solution of borane:tetrahydrofurane complex (1M, 100 mL) was added dropwise over 1 hour to a cold (0 C.) suspension of DL-3-amino-3-(4-fluorophenyl)propionoc acid (7.30 g, 39.9 mmol) in THF (40 mL). The mixture was heated to reflux for 22 hours. The mixture was then cooled to 0 C. and methanol (35 mL) was added over 15 minutes. The mixture was then heated to reflux for 30 minutes and concentrated to a thick oil. The oil was coevaporated 3 times with methanol (50 mL). The crude product was used directly in next step. The oil that was obtained in the previous step was dissolved in water and added dropwise to concentrated HBr (44 mL) The solution was heated at reflux for 18 hours. It was then concentrated to dryness (11.58 g). The solid was suspended in hot heptane/2-butanone then cooled to room temperature. Ether was added and the mixture was stirred for 30 minutes. The solid was collected by filtration and rinsed with ether (9.97 g, about 66% for two steps). The 3-bromo-1-(4-fluorophenyl)-1-propylamine hydrobromide (obtained in step 2, 32 mmol) was added to a solution of sodium sulfite (3.78 g, 30 mmol) in water (40 mL). The mixture was heated at 90 C. for 2.5 hours, and was then concentrated to a thick paste. Concentrated HCl (8 mL) was added to the paste. The resulting suspension was stirred for 20 minutes at room temperature. The solid was collected by filtration and rinsed with concentrated HCl (330 mL). The filtrated solid was concentrated to dryness. The solid was washed in ethanol/toluene then dried in vacuo (3.79 g). The solid was recrystallized in ethanol (25 mL) and water (6 mL). After cooling to room temperature, the solid was collected by filtration, rinsed with ethanol (25 mL) and dried overnight at 60 C. in a vacuum oven. The title compounds was obtained as a fine white crystalline solid, yield 2.37 g, 26% overall yield. 1H NMR 1H (500 MHz, D2O) delta 2.22-2.36 (m, 2H), 2.54-2.60 (m, 1H), 2.65-2.71(m, 1H), 4.37-4.40 (m, 1H), 7.07 (t, J=8.5 Hz, 2H), 7.26-7.31 (dd, J=8.3, 5.4 Hz, 2H); 13C (125 MHz, D2O) delta 28.82, 47.1, 53.5, 116.4 (d, J=22 Hz, 2C), 139.7 (d, J=11.6 Hz, 2C), 130.9, 163.2 (d, J=246 Hz, 2C); 19F (282 MHz, D2O) -112.9 to -113.0 (m); ES-MS 232 (M-1).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3685 - 3690
[2]Patent: US2006/183800,2006,A1.Location in patent: Page/Page column 67-68

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Code	Phrase
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Ghs Hazard Statements

Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere