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Quality Control of [ 1160247-07-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1160247-07-3 ]

CAS No. :	1160247-07-3	MDL No. :	MFCD11227083
Formula :	C₁₃H₂₂N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	270.33	Pubchem ID :	-
Synonyms :

Safety of [ 1160247-07-3 ]

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

Application In Synthesis of [ 1160247-07-3 ]

* 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 [ 1160247-07-3 ]
Downstream synthetic route of [ 1160247-07-3 ]

[ 1160247-07-3 ] Synthesis Path-Upstream 1~1

1
[ 1160247-07-3 ]
[ 930785-40-3 ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: With dimethylsulfide borane complex In tetrahydrofuran at 25 - 70℃; for 16 h; Stage #2: With N,N`-dimethylethylenediamine In methanol at 70℃; for 16 h;	This reaction was carried out in 12 batches, as follows. Borane-dimethyl sulfide complex (10 M in dimethyl sulfide, 75 mL, 750 mmol) was added in a drop-wise manner to a solution of C22 (50 g, 180 mmol) in tetrahydrofuran (1.5 L). The reaction mixture was heated at reflux (70 °C) for 6 hours and subsequently allowed to stir at 25 °C for 10 hours. It was then quenched with methanol (500 mL), stirred for 30 minutes at 25 °C, and concentrated under reduced pressure. The resulting white solid was dissolved in methanol (1 L), treated with Ν,Ν'- dimethylethane-1 ,2-diamine (65 g, 740 mmol), and heated at reflux (70 °C) for 16 hours. The 12 reaction mixtures were combined and concentrated in vacuo to provide a light yellow oil; this was dissolved in dichloromethane (4 L), washed with aqueous ammonium chloride solution (4 x 2 L), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was triturated with petroleum ether (500 mL) at 25 °C for 30 minutes to provide the product (304 g) as a white solid. The filtrate from the trituration was concentrated in vacuo, and the residue was triturated with petroleum ether (200 mL) at 25 °C for 36 hours, affording additional product (135 g) as a white solid. Combined yield: 439 g, 1.71 mol, 77percent. LCMS m/z 257.2 [M+H]⁺. ¹ H NMR (400 MHz, CDCI₃) δ 3.85-3.59 (m, 4H), 3.14 (br dd, J=1 1 , 1 1 Hz, 2H), 2.84 (dd, J=4.9, 4.6 Hz, 2H), 2.68 (s, 2H), 2.02-1.84 (br m, 2H), 1.47-1.33 (m, 2H), 1.45 (s, 9H).
77%	Stage #1: With dimethylsulfide borane complex In tetrahydrofuran at 25 - 70℃; for 16 h; Stage #2: With N,N`-dimethylethylenediamine In tetrahydrofuran; methanol at 70℃; for 16 h;	This reaction was carried out in 12 batches, asfollows. Borane-dimethyl sulfide complex (10 M in dimethylsulfide, 75 mL, 750 mmol) was added in a drop-wisemanner to a solution of C2 (50 g, 180 mmol) in tetrahydrofuran(1.5 L). The reaction mixture was heated at reflux (70°C.) for 6 hours and subsequently allowed to stir at 25° C. for10 hours. It was then quenched with methanol (500 mL),stirred for 30 minutes at 25° C., and concentrated underreduced pressure. The resulting white solid was dissolved inmethanol (1 L), treated with N,N'-dimethylethane-1,2-diamine(65 g, 740 mmol), and heated at reflux (70° C.) for 16hours. The 12 reaction mixtures were combined and concentratedin vacuo to provide a light yellow oil; this wasdissolved in dichloromethane (4 L), washed with aqueousammonium chloride solution (4x2 L), dried over sodiumsulfate, filtered, and concentrated under reduced pressure.The residue was triturated with petroleum ether (500 mL) at25° C. for 30 minutes to provide the product (304 g) as awhite solid. The filtrate from the trituration was concentratedin vacuo, and the residue was triturated with petroleum ether(200 mL) at 25° C. for 36 hours, affording additional product(135 g) as a white solid. Combined yield: 439 g, 1.71 mol,77percent. LCMS m/z 257.2 [M+Ht. 1H NMR (400 MHz,CDC13 ) o 3.85-3.59 (m, 4H), 3.14 (br dd, 1=11, 11 Hz, 2H),2.84 (dd, 1=4.9, 4.6 Hz, 2H), 2.68 (s, 2H), 2.02-1.84 (br m,2H), 1.47-1.33 (m, 2H), 1.45 (s, 9H).
65%	Stage #1: With dimethylsulfide borane complex In tetrahydrofuran at 55℃; for 2 h; Stage #2: With N,N`-dimethylethylenediamine In methanolReflux	Intermediate 9A: tert-butyl I -oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate To a solution of intermediate 3G (1.50 g, 5.55 mmol) in THE (19 mL), borane-dimethyl sulfide complex (1.67 mL, 16.6 mmol) was added dropwise at r.t.. The reactionmixture was stirred at 55 00 for 2 h, then it was cooled to r.t.. MeOH was added dropwise and the solvent was concentrated under vacuum. The obtained residue was dissolved in methanol (20 mL), N,W-dimethylethylenediamine (3.0 mL, 28.3 mmol) was added and the mixture was stirred under reflux overnight. After cooling to r.t., the volatiles were removed under vacuum, and the residue was purified by flashchromatography, silica gel, gradient dichloromethane to methanol:dichloromethane (1:4) to give the title compound (0.928 g, 65percent yield). HPLC retention time: 2.91 mm; MS: 257 (M+H).

0.928 g

Stage #1: With dimethylsulfide borane complex In tetrahydrofuran at 55℃; for 2 h;
Stage #2: With N,N`-dimethylethylenediamine In methanolReflux

To a solution of intermediate 3A (1.50 g, 5.55 mmol) in THF (19 mL), borane-dimethyl sulfide complex (1.67 mL, 16.6 mmol) was added dropwise at r.t. The reaction mixture was stirred at 55 °C for 2 h, then it was cooled to r.t.. MeOH was carefully added and the solvent was concentrated under vacuum. The residue was dissolved in methanol (20 mL), A/.A/'-dimethylethylenediamine (3.0 mL, 28.3 mmol) was added and the mixture was stirred under reflux overnight. After cooling to r.t., the volatiles were removed under vacuum, and the residue was purified by flash chromatography, silica gel, gradient dichloromethane to methanokdichloromethane (1 :4) to give the title compound (0.928 g, 65percent yield). HPLC retention time: 2.91 min; MS: 257 (M+H).

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7458 - 7461
[2] Patent: WO2017/21805, 2017, A1, . Location in patent: Page/Page column 83; 85
[3] Patent: US2018/208608, 2018, A1, . Location in patent: Paragraph 0243; 0244; 0246
[4] Patent: WO2015/185207, 2015, A1, . Location in patent: Page/Page column 190; 191
[5] Patent: WO2015/185208, 2015, A1, . Location in patent: Page/Page column 147; 148
[6] Patent: WO2016/65582, 2016, A1, . Location in patent: Page/Page column 49
[7] Patent: WO2016/122994, 2016, A1, . Location in patent: Page/Page column 47

[ 1160247-07-3 ] Synthesis Path-Downstream 1~4

1
[ 392331-66-7 ]
[ 79-04-9 ]
[ 1160247-07-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7458 - 7461

2
[ 1160247-07-3 ]
[ 930785-40-3 ]

Yield	Reaction Conditions	Operation in experiment
77%		This reaction was carried out in 12 batches, as follows. Borane-dimethyl sulfide complex (10 M in dimethyl sulfide, 75 mL, 750 mmol) was added in a drop-wise manner to a solution of C22 (50 g, 180 mmol) in tetrahydrofuran (1.5 L). The reaction mixture was heated at reflux (70 C) for 6 hours and subsequently allowed to stir at 25 C for 10 hours. It was then quenched with methanol (500 mL), stirred for 30 minutes at 25 C, and concentrated under reduced pressure. The resulting white solid was dissolved in methanol (1 L), treated with Nu,Nu'- dimethylethane-1 ,2-diamine (65 g, 740 mmol), and heated at reflux (70 C) for 16 hours. The 12 reaction mixtures were combined and concentrated in vacuo to provide a light yellow oil; this was dissolved in dichloromethane (4 L), washed with aqueous ammonium chloride solution (4 x 2 L), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was triturated with petroleum ether (500 mL) at 25 C for 30 minutes to provide the product (304 g) as a white solid. The filtrate from the trituration was concentrated in vacuo, and the residue was triturated with petroleum ether (200 mL) at 25 C for 36 hours, affording additional product (135 g) as a white solid. Combined yield: 439 g, 1.71 mol, 77%. LCMS m/z 257.2 [M+H]+. 1 H NMR (400 MHz, CDCI3) delta 3.85-3.59 (m, 4H), 3.14 (br dd, J=1 1 , 1 1 Hz, 2H), 2.84 (dd, J=4.9, 4.6 Hz, 2H), 2.68 (s, 2H), 2.02-1.84 (br m, 2H), 1.47-1.33 (m, 2H), 1.45 (s, 9H).
77%		This reaction was carried out in 12 batches, asfollows. Borane-dimethyl sulfide complex (10 M in dimethylsulfide, 75 mL, 750 mmol) was added in a drop-wisemanner to a solution of C2 (50 g, 180 mmol) in tetrahydrofuran(1.5 L). The reaction mixture was heated at reflux (70C.) for 6 hours and subsequently allowed to stir at 25 C. for10 hours. It was then quenched with methanol (500 mL),stirred for 30 minutes at 25 C., and concentrated underreduced pressure. The resulting white solid was dissolved inmethanol (1 L), treated with N,N'-dimethylethane-1,2-diamine(65 g, 740 mmol), and heated at reflux (70 C.) for 16hours. The 12 reaction mixtures were combined and concentratedin vacuo to provide a light yellow oil; this wasdissolved in dichloromethane (4 L), washed with aqueousammonium chloride solution (4x2 L), dried over sodiumsulfate, filtered, and concentrated under reduced pressure.The residue was triturated with petroleum ether (500 mL) at25 C. for 30 minutes to provide the product (304 g) as awhite solid. The filtrate from the trituration was concentratedin vacuo, and the residue was triturated with petroleum ether(200 mL) at 25 C. for 36 hours, affording additional product(135 g) as a white solid. Combined yield: 439 g, 1.71 mol,77%. LCMS m/z 257.2 [M+Ht. 1H NMR (400 MHz,CDC13 ) o 3.85-3.59 (m, 4H), 3.14 (br dd, 1=11, 11 Hz, 2H),2.84 (dd, 1=4.9, 4.6 Hz, 2H), 2.68 (s, 2H), 2.02-1.84 (br m,2H), 1.47-1.33 (m, 2H), 1.45 (s, 9H).
65%		Intermediate 9A: tert-butyl I -oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate To a solution of intermediate 3G (1.50 g, 5.55 mmol) in THE (19 mL), borane-dimethyl sulfide complex (1.67 mL, 16.6 mmol) was added dropwise at r.t.. The reactionmixture was stirred at 55 00 for 2 h, then it was cooled to r.t.. MeOH was added dropwise and the solvent was concentrated under vacuum. The obtained residue was dissolved in methanol (20 mL), N,W-dimethylethylenediamine (3.0 mL, 28.3 mmol) was added and the mixture was stirred under reflux overnight. After cooling to r.t., the volatiles were removed under vacuum, and the residue was purified by flashchromatography, silica gel, gradient dichloromethane to methanol:dichloromethane (1:4) to give the title compound (0.928 g, 65% yield). HPLC retention time: 2.91 mm; MS: 257 (M+H).

0.928 g		To a solution of intermediate 3A (1.50 g, 5.55 mmol) in THF (19 mL), borane-dimethyl sulfide complex (1.67 mL, 16.6 mmol) was added dropwise at r.t. The reaction mixture was stirred at 55 C for 2 h, then it was cooled to r.t.. MeOH was carefully added and the solvent was concentrated under vacuum. The residue was dissolved in methanol (20 mL), A/.A/'-dimethylethylenediamine (3.0 mL, 28.3 mmol) was added and the mixture was stirred under reflux overnight. After cooling to r.t., the volatiles were removed under vacuum, and the residue was purified by flash chromatography, silica gel, gradient dichloromethane to methanokdichloromethane (1 :4) to give the title compound (0.928 g, 65% yield). HPLC retention time: 2.91 min; MS: 257 (M+H).
		To a solution of tert-butyl 3-oxo-1-oxa-4, 9-diazaspiro [5.5] undecane-9-carboxylate (16.0 g, 60 mmol) in THF (70 mL) was added tetrahydrofuran-borane (250 mL, 250 mmol) at room temperature. The reaction mixture was refluxed for 2 h and the solvent was removed under the reduced presure. To the resulting mixture was added MeOH and N1, N1, N2, N2-tetramethylethane-1, 2-diamine and the reaction was stirred at 78 overnight. The reaction was concentrated and the residue was diluted with EtOAc and water. The organic layer was separated, washed with brine, and concentrated in vacuo to give tert-butyl 1-oxa-4, 9-diazaspiro [5.5] undecane-9-carboxylate. 1H NMR (300 MHz, CDCl3) delta : 1.45 (s, 9H) , 1.61 (s, 2H) , 1.93 (d, J 12.0 Hz, 2H) , 2.67 (s, 2H) 2.83 (m, 2H) , 3.16 (t, J1 9.0 Hz, J2 12.0 Hz, 2H) 3.65 (m, 4H) .
		To a solution of tert-butyl 3-oxo-l-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (16.0 g, 60 mmol) in THF (70 mL) was added tetrahydrofuran-borane (250 mL, 250 mmol) at room temperature. The reaction mixture was refluxed for 2 h and the solvent was removed under the reduced presure. To the resulting mixture was added MeOH and Ni,Ni,N2,N2-tetramethylethane-l,2-diamine and the reaction was stirred at 78C overnight. The reaction was concentrated and the residue was diluted with EtOAc and water. The organic layer was separated, washed with brine, and concentrated in vacuo to give tert-butyl l-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate. 1H MR (300 MHz, CDC13) delta: 1.45 (s, 9H), 1.61 (s, 2H), 1.93 (d, J= 12.0 Hz, 2H), 2.67 (s, 2H) 2.83 (m, 2H), 3.16 (t, Jj = 9.0 Hz, J2 = 12.0 Hz, 2H) 3.65 (m, 4H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7458 - 7461
[2]Patent: WO2017/21805,2017,A1 .Location in patent: Page/Page column 83; 85
[3]Patent: US2018/208608,2018,A1 .Location in patent: Paragraph 0243; 0244; 0246
[4]Patent: WO2015/185207,2015,A1 .Location in patent: Page/Page column 190; 191
[5]Patent: WO2015/185208,2015,A1 .Location in patent: Page/Page column 147; 148
[6]Patent: WO2016/65582,2016,A1 .Location in patent: Page/Page column 49
[7]Patent: WO2016/122994,2016,A1 .Location in patent: Page/Page column 47

3
[ 392331-66-7 ]
[ 1160247-07-3 ]

Reference： [1]Patent: WO2015/185207,2015,A1
[2]Patent: WO2015/185208,2015,A1
[3]Patent: WO2016/65582,2016,A1
[4]Patent: WO2016/122994,2016,A1
[5]Patent: WO2017/21805,2017,A1
[6]Patent: US2018/208608,2018,A1

4
[ 1160247-07-3 ]
[ 1352926-03-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: dimethylsulfide borane complex / tetrahydrofuran / 2 h / 55 °C 1.2: Reflux 2.1: acetic acid / tetrahydrofuran / 0.25 h / 20 °C 2.2: 20 °C
	Multi-step reaction with 2 steps 1.1: dimethylsulfide borane complex / tetrahydrofuran / 16 h / 25 - 70 °C 1.2: 16 h / 70 °C 2.1: magnesium sulfate; sodium cyanoborohydride; triethylamine / 30 h / 28 - 45 °C 2.2: 16 h / 45 °C

Reference： [1]Current Patent Assignee: Corporacion Quimico Farmaceutica Esteve SA - WO2015/185207, 2015, A1
[2]Current Patent Assignee: PFIZER INC - US2018/208608, 2018, A1

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H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1160247-07-3 ] {[proInfo.proName]}

Quality Control of [ 1160247-07-3 ]

Related Doc. of [ 1160247-07-3 ]

Product Details of [ 1160247-07-3 ]

Safety of [ 1160247-07-3 ]

Application In Synthesis of [ 1160247-07-3 ]

[ 1160247-07-3 ] Synthesis Path-Upstream 1~1

[ 1160247-07-3 ] Synthesis Path-Downstream 1~4

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