[ CAS No. 1446333-79-4 ] {[proInfo.proName]}

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Quality Control of [ 1446333-79-4 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1446333-79-4 ]

CAS No. :	1446333-79-4	MDL No. :	MFCD28397290
Formula :	C₁₁H₆BrFO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	285.07	Pubchem ID :	-
Synonyms :

Safety of [ 1446333-79-4 ]

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Application In Synthesis of [ 1446333-79-4 ]

* 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 [ 1446333-79-4 ]

[ 1446333-79-4 ] Synthesis Path-Downstream 1~14

1
[ 1211590-31-6 ]
[ 1446333-79-4 ]
[ 1446333-80-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	In ethanol; at 95.0℃; for 18.0h;	Step A: A mixture of 3-(2-bromoacetyl)-7-fluoro-2H-chromen-2-one (500 mg, 1.75 mmol), <strong>[1211590-31-6]3-fluoro-5-methylpyridin-2-amine</strong> (240 mg, 1.9 mmol) and EtOH (3 mL) was heated at 95 C for 18 h. The reaction mixture was partitioned between CH2CI2 and aqueous K2C03. The organic layer was dried over MgS04, filtered, and concentrated under vacuum. The residue was triturated with 1 : 1 hexane/acetone, yielding 7-fluoro-3-(8-fluoro-6-methylimidazo[l,2-a]pyridin- 2-yl)-2H-chromen-2-one (412 mg, 75%) as an orange solid. 1H NMR (500 MHz, CDC13): delta 8.85 (1H, s), 8.50 (1H, d, J= 2.5 Hz), 7.77 (1H, m), 7.63 (1H, dd, J= 9Hz, 6 Hz), 7.11 (1H, dd, J= 9 Hz, 2 Hz), 7.07 (1H, td, J= 8.5 Hz, 2.5 Hz), 6.80 (1H, d, J= 6 Hz), 2.34 (3H, s).
75%	In ethanol; at 95.0℃; for 18.0h;	Step A: A mixture of 3-(2-bromoacetyl)-7-fluoro-2H-chromen-2-one (500 mg, 1.75 mmol), <strong>[1211590-31-6]3-fluoro-5-methylpyridin-2-amine</strong> (240 mg, 1.9 mmol) and EtOH (3 mL) was heated at 95 C. for 18 h. The reaction mixture was partitioned between CH2Cl2 and aqueous K2CO3. The organic layer was dried over MgSO4, filtered, and concentrated under vacuum. The residue was triturated with 1:1 hexane/acetone, yielding 7-fluoro-3-(8-fluoro-6-methylimidazo[1,2-a]pyridin-2-yl)-2H-chromen-2-one (412 mg, 75%) as an orange solid. 1H NMR (500 MHz, CDCl3): delta 8.85 (1H, s), 8.50 (1H, d, J=2.5 Hz), 7.77 (1H, m), 7.63 (1H, dd, J=9 Hz, 6 Hz), 7.11 (1H, dd, J=9 Hz, 2 Hz), 7.07 (1H, td, J=8.5 Hz, 2.5 Hz), 6.80 (1H, d, J=6 Hz), 2.34 (3H, s).

Reference： [1]Patent: WO2013/101974,2013,A1 .Location in patent: Paragraph 00798; 00799
[2]Patent: US9617268,2017,B2 .Location in patent: Page/Page column 367; 368

2
[ 1211590-31-6 ]
[ 1446333-79-4 ]
[ 1446331-60-7 ]

Reference： [1]Patent: WO2013/101974,2013,A1

3
[ 1318770-38-5 ]
[ 1446333-79-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	With bromine In chloroform at 20℃; for 1h;	36.2.B Step B: Step B: Into a solution of 3-acetyl-7-fluoro-2H-chromen-2-one (1.96 g, 9.5 mmol) in CHC13 (20 mL) was added dropwise a solution of bromine (1.6 g, 10 mmol) in CHC13 (10 mL). The mixture was stirred at room temperature for 1 h and filtered. The solid was washed with CHC13 and dried to give the title compound (1.96 g, 72%) as a pale yellow solid. 1H NMR (500 MHz, CDC13): δ 8.63 (1H, s), 7.72 (1H, m), 7.17-7.10 (2H, m), 4.73 (2H, s).
72%	With bromine In chloroform at 20℃; for 1h;
72%	With bromine In chloroform at 20℃; for 1h;	36.2.B Step B: Into a solution of 3-acetyl-7-fluoro-2H-chromen-2-one (1.96 g, 9.5 mmol) in CHCl3 (20 mL) was added dropwise a solution of bromine (1.6 g, 10 mmol) in CHCl3 (10 mL). The mixture was stirred at room temperature for 1 h and filtered. The solid was washed with CHCl3 and dried to give the title compound (1.96 g, 72%) as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 8.63 (1H, s), 7.72 (1H, m), 7.17-7.10 (2H, m), 4.73 (2H, s).

Reference： [1]Current Patent Assignee: PTC THERAPEUTICS INC; ROCHE HOLDING AG - WO2013/101974, 2013, A1 Location in patent: Paragraph 00795; 00797
[2]Woll, Matthew G.; Qi, Hongyan; Turpoff, Anthony; Zhang, Nanjing; Zhang, Xiaoyan; Chen, Guangming; Li, Chunshi; Huang, Song; Yang, Tianle; Moon, Young-Choon; Lee, Chang-Sun; Choi, Soongyu; Almstead, Neil G.; Naryshkin, Nikolai A.; Dakka, Amal; Narasimhan, Jana; Gabbeta, Vijayalakshmi; Welch, Ellen; Zhao, Xin; Risher, Nicole; Sheedy, Josephine; Weetall, Marla; Karp, Gary M. [Journal of Medicinal Chemistry, 2016, vol. 59, # 13, p. 6070 - 6085]
[3]Current Patent Assignee: PTC THERAPEUTICS INC; ROCHE HOLDING AG - US9617268, 2017, B2 Location in patent: Page/Page column 367

4
[ 91678-81-8 ]
[ 1446333-79-4 ]
3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-fluoro-2H-chromen-2-one hydrobromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In acetonitrile at 120℃; for 0.333333h; Sealed tube;
90%	In acetonitrile at 120℃; for 0.333333h; Sealed tube;	43.A Step A: A mixture of 3-(2-bromoacetyl)-7-fluoro-2H-chromen-2-one (0.684 g, 2.4 mmol, prepared in Example 36, Part 2) and 3,5-dimethylpyrazin-2-amine (0.246 g, 2.0 mmol) in CH3CN (10 mL) was stirred at 120° C. in a sealed tube for 20 min. The mixture was cooled to room temperature and diluted with Et2O to produce a precipitate. The solid was collected by vacuum filtration, washed with Et2O and dried to give 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-fluoro-2H-chromen-2-one hydrobromide (0.7 g, 90%) as a tan solid. MS m/z 310.1 [M+H]+.

Reference： [1]Woll, Matthew G.; Qi, Hongyan; Turpoff, Anthony; Zhang, Nanjing; Zhang, Xiaoyan; Chen, Guangming; Li, Chunshi; Huang, Song; Yang, Tianle; Moon, Young-Choon; Lee, Chang-Sun; Choi, Soongyu; Almstead, Neil G.; Naryshkin, Nikolai A.; Dakka, Amal; Narasimhan, Jana; Gabbeta, Vijayalakshmi; Welch, Ellen; Zhao, Xin; Risher, Nicole; Sheedy, Josephine; Weetall, Marla; Karp, Gary M. [Journal of Medicinal Chemistry, 2016, vol. 59, # 13, p. 6070 - 6085]
[2]Current Patent Assignee: PTC THERAPEUTICS INC; ROCHE HOLDING AG - US9617268, 2017, B2 Location in patent: Page/Page column 375; 376

5
[ 1446333-79-4 ]
[ 19842-07-0 ]
C₁₈H₁₃FN₂O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 6070 - 6085

6
[ 5521-58-4 ]
[ 1446333-79-4 ]
C₁₆H₁₀FN₃O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 6070 - 6085

7
[ 1446333-79-4 ]
[ 14667-55-1 ]
1-(2-(7-fluoro-2-oxo-2H-chromen-3-yl)-2-oxoethyl)-2,3,5-trimethylpyrazin-1-ium bromide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 6070 - 6085

8
[ 50840-23-8 ]
[ 1446333-79-4 ]
7-fluoro-3-(6-methylimidazo[1,2-a]pyrimidin-2-yl)-2H-chromen-2-one hydrobromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	In ethanol; at 95℃; for 16h;	Step A: Following the procedure in Example 36, Part 3, 3-(2-bromoacetyl)-7-fluoro-2H-chromen-2-one (0.855 g, 3.0 mmol) and <strong>[50840-23-8]5-methylpyrimidin-2-amine</strong> (0.327 g, 3.0 mmol) in EtOH (6.0 mL) gave 7-fluoro-3-(6-methylimidazo[1,2-a]pyrimidin-2-yl)-2H-chromen-2-one hydrobromide (0.37 g, 42%) as a pale yellow solid. MS m/z 296.2 [M+H]+.

Reference： [1]Patent: US9617268,2017,B2 .Location in patent: Page/Page column 371; 372

9
[ 1446333-79-4 ]
[ 1683-85-8 ]
7-fluoro-3-(6-fluoroimidazo[1,2-a]pyrimidin-2-yl)-2H-chromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In ethanol; at 95℃; for 16h;	Step A: Following the procedure in Example 36, Part 3, 3-(2-bromoacetyl)-7-fluoro-2H-chromen-2-one (1.32 g, 4.1 mmol) and <strong>[1683-85-8]<strong>[1683-85-8]5-fluoropyrimidin-2-amin</strong>e</strong> (0.465 g, 4.1 mmol) in EtOH (12.0 mL) gave 7-fluoro-3-(6-fluoroimidazo[1,2-a]pyrimidin-2-yl)-2H-chromen-2-one (0.85 g, 70%) as a pale yellow solid. MS m/z 300.1 [M+H]+.

Reference： [1]Patent: US9617268,2017,B2 .Location in patent: Page/Page column 372; 373

10
[ 39136-60-2 ]
[ 1446333-79-4 ]
3-(2-ethylimidazo[2,1-b]thiazol-6-yl)-7-fluoro-2H-chromen-2-one hydrobromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	In ethanol; at 95℃; for 20h;	Step A: Following the procedure in Example 41, Step A, 3-(2-bromoacetyl)-7-fluoro-2H-chromen-2-one (0.76 g, 2.7 mmol) and <strong>[39136-60-2]5-ethylthiazol-2-amine</strong> (0.35 g, 2.7 mmol) in EtOH (20 mL) gave 3-(2-ethylimidazo[2,1-b]thiazol-6-yl)-7-fluoro-2H-chromen-2-one hydrobromide (0.55 g, 66%) as a tan solid. MS m/z 315.2 [M+H]+.

Reference： [1]Patent: US9617268,2017,B2 .Location in patent: Page/Page column 375

11
[ 18591-87-2 ]
[ 1446333-79-4 ]
7-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-3-(6-methylimidazo[1,2-b]pyridazin-2-yl)-2H-chromen-2-one [ No CAS ]

Reference： [1]Patent: US9617268,2017,B2

12
[ 18591-87-2 ]
[ 1446333-79-4 ]
7-fluoro-3-(6-methylimidazo[1,2-b]pyridazin-2-yl)-2H-chromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In acetonitrile; at 100℃; for 5h;	Step B: A mixture of 3-(2-bromoacetyl)-7-fluoro-2H-chromen-2-one (900 mg, 3.0 mmol, prepared in Example 36, Part 2) and <strong>[18591-87-2]6-methylpyridazin-3-amine</strong> (330 mg, 3.0 mmol) was stirred in CH3CN (6.0 mL) at 100 C. for 5 h, then the solvent was removed. The residue was purified by silica gel column chromatography (5% MeOH in CH2Cl2) to give 7-fluoro-3-(6-methylimidazo[1,2-b]pyridazin-2-yl)-2H-chromen-2-one (814 mg, 92%) as a tan solid. MS m/z 296.0 [M+H]+.

Reference： [1]Patent: US9617268,2017,B2 .Location in patent: Page/Page column 386; 387

13
[ 1632-74-2 ]
[ 1446333-79-4 ]
1-(2-(7-fluoro-2-oxo-2H-chromen-3-yl)-2-oxoethyl)-3,6-dimethylpyridazin-1-ium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; at 20℃; for 120h;Sealed tube;	Step B: A mixture of <strong>[1632-74-2]3,6-dimethylpyridazine</strong> (81 mg, 0.75 mmol) and 3-(2-bromoacetyl)-7-fluoro-2H-chromen-2-one (143 mg, 0.5 mmol, prepared in Example 36, Part 2) in anhydrous CH3CN (1 mL) was stirred at room temperature for 5 d in a sealed tube to afford 1-(2-(7-fluoro-2-oxo-2H-chromen-3-yl)-2-oxoethyl)-3,6-dimethylpyridazin-1-ium bromide as a crude mixture in CH3CN.

Reference： [1]Patent: US9617268,2017,B2 .Location in patent: Page/Page column 395; 396

14
[ 1632-74-2 ]
[ 1446333-79-4 ]
7-fluoro-3-(2-methylpyrrolo[1,2-b]pyridazin-6-yl)-2H-chromen-2-one [ No CAS ]

Reference： [1]Patent: US9617268,2017,B2

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[ CAS No. 1446333-79-4 ] {[proInfo.proName]}

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[ 1446333-79-4 ] Synthesis Path-Downstream 1~14

Precautionary Statements-General

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