[ CAS No. 111511-90-1 ] {[proInfo.proName]}

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Quality Control of [ 111511-90-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 111511-90-1 ]

Product Details of [ 111511-90-1 ]

CAS No. :	111511-90-1	MDL No. :	MFCD19313175
Formula :	C₇H₈N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	136.15	Pubchem ID :	-
Synonyms :

Safety of [ 111511-90-1 ]

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Application In Synthesis of [ 111511-90-1 ]

* 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 [ 111511-90-1 ]
Downstream synthetic route of [ 111511-90-1 ]

[ 111511-90-1 ] Synthesis Path-Upstream 1~1

1
[ 111511-90-1 ]
[ 5337-04-2 ]

Reference： [1] Patent: US4870070, 1989, A,

[ 111511-90-1 ] Synthesis Path-Downstream 1~4

1
[ 111511-90-1 ]
[ 5337-04-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol; water;	EXAMPLE 4 Tetrahydro-4H-pyran-4,4-dicarboxylic acid, disilver (1+)salt A mixture of 20.4 g of tetrahydro-4H-pyran-4,4-dicarbonitrile, 45 ml of 10N sodium hydroxide and 225 ml of ethanol in 105 ml of water was heated at reflux for 5 hours. Then the solution was evaporated to dryness. The residue was dissolved in 50 ml of water and the solution was adjusted to pH 1.5 with nitric acid. The solution was cooled in an ice bath then kept at room temperature for 16 hours. The crystallized product was collected by filtration, washed with water and dried to give 8.44 g of tetrahydro-4H-pyran-4,4-dicarboxylic acid as white crystals, mp 155 C. (dec.).

Reference： [1]Patent: US4870070,1989,A

2
[ 111511-90-1 ]
[ 1263374-32-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; ethanol at 20℃; for 4h;	2 Step 2; A mixture of dihydro-2H-pyran-4,4(3H)-dicarbonitrile (450 mg, 3.31 mmol) and Sodium borohydride (375 mg, 9.92 mmol) in EtOH (15 ml) was stirred at ambient temperature for about 4 hours. The mixture was concentrated and the resulting residue was diluted with ethyl acetate, washed with water and dried. Concentration in vacuo afforded 388 mg of the crude product which was used directly in the next step. LCMS (m/z): 141.0 [M+H]+; Retention time=0.18 min.
	Stage #1: dihydro-2H-pyran-4,4(3H)-dicarbonitrile With sodium tetrahydroborate In ethanol at 20℃; for 4h; Stage #2: With water In ethyl acetate	To a solution of dihydro-2H-pyran-4,4(3H)-dicarbonitrile (450 mg, 3.31 mmol in EtOH (15 mL) was added sodium borohydride (375 mg, 9.92 mmol) in portions and the mixture was stirred at room temperature for 4 hrs. The mixture was concentrated under reduced pressure and the residue was diluted with EtOAc (30 mL), washed with water (10 mL), dried over sodium sulfate, filtered off and concentrated under reduced pressure providing crude 4-(aminomethyl)tetrahydro-2H-pyran-4-carbonitrile (388mg), which was directly used in the next step without further purification. LCMS (m/z): 141.0[M+H]+; Rt = 0.18 min.
	With sodium tetrahydroborate In ethanol at 20℃; for 4h;	2 To a solution of dihydro-2H-pyran-4,4(3H)-dicarbonitrile (450 mg, 3.31 mmol in EtOH (15 mL) was added sodium borohydride (375 mg, 9.92 mmol) in portions and the mixture was stirred at room temperature for 4 hrs. The mixture was concentrated under reduced pressure and the residue was diluted with EtOAc (30 mL), washed with water (10 mL), dried over sodium sulfate, filtered off and concentrated under reduced pressure providing crude 4-(aminomethyl)tetrahydro- 2H-pyran-4-carbonitrile (388 mg), which was directly used in the next step without further purification. LCMS (m/z): 141.0 [M+H]+; Retention time = 0.18 min.

	With sodium tetrahydroborate In ethanol at 20℃; for 4h;	2 To a solution of dihydro-2H-pyran-4,4(3H)-dicarbonitrile (450 mg, 3.31 mmol in EtOH (15 mL) was added sodium borohydride (375 mg, 9.92 mmol) in portions and the mixture was stirred at room temperature for 4 hrs. The mixture was concentrated under reduced pressure and the residue was diluted with EtOAc (30 mL), washed with water (10 mL), dried over sodium sulfate, filtered off and concentrated under reduced pressure providing crude 4-(aminomethyl)tetrahydro-2H-pyran-4-carbonitrile (388 mg), which was directly used in the next step without further purification. LCMS (m/z): 141.0 [M+H]+;Retention time = 0.18 min.
	With sodium tetrahydroborate In ethanol at 20℃; for 4h;	2 To a solution of dihydro-2H-pyran-4,4(3H)-dicarbonitrile (450 mg, 3.31 mmol inEtOH (15 mL) was added sodium borohydride (375 mg, 9.92 mmol) in portions and the mixture was stirred at room temperature for 4 hrs. The mixture was concentrated under reduced pressure and the residue was diluted with EtOAc (30 mL), washed with water (10 mL), dried over sodium sulfate, filtered off and concentrated under reduced pressure providing crude 4-(aminomethyl)tetrahydro-2H-pyran-4-carbonitrile (388mg), which was directly used in the next step without further purification. LCMS (m/z): 141.0 [M+H]+; Rt = 0.18 min.
	With sodium tetrahydroborate In ethanol at 20℃; for 4h;	2 To a solution of dihydro-2H-pyran-4,4(3H)-dicarbonitrile (450 mg, 3.31 mmol in EtOH (15 ml_) was added sodium borohydride (375 mg, 9.92 mmol) in portions and the mixture was stirred at room temperature for 4 hrs. The mixture was concentrated under reduced pressure and the residue was diluted with EtOAc (30 ml_), washed with water (10 ml_), dried over sodium sulfate, filtered off and concentrated under reduced pressure providing crude 4-(aminomethyl)tetrahydro-2H-pyran-4-carbonitrile (388 mg), which was directly used in the next step without further purification. LCMS (m/z): 141.0 [M+H]+; Retention time = 0.18 min.
	With sodium tetrahydroborate; ethanol at 20℃; for 4h;	Step 2. A mixture of dihydro-2H-pyran-4,4(3H)-dicarbonitrile (450 mg, 3.31 mmol) and Sodium borohydride (375 mg, 9.92 mmol) in EtOH (15 ml) was stirred at ambient temperature for about 4 hours. The mixture was concentrated and the resulting residue was diluted with ethyl acetate, washed with water and dried. Concentration in vacuo afforded 388 mg of the crude product which was used directly in the next step. LCMS (m/z): 141.0 [M+H]+; Retention time = 0.18 min.
	With sodium tetrahydroborate In ethanol at 20℃; for 4h;	2 To a solution of dihydro-2H-pyran-4,4(3H)-dicarbonitrile (450 mg, 3.31 mmol in EtOH(15 mL) was added sodium borohydride (375 mg, 9.92 mmol) in portions and the mixture was stirred at room temperature for 4 hrs. The mixture was concentrated under reduced pressure and the residue was diluted with EtOAc (30 mL), washed with water (10 mL), dried over sodium sulfate, filtered off and concentrated under reduced pressure providing crude 4- (aminomethyl)tetrahydro-2H-pyran-4-carbonitrile (388mg), which was directly used in the next step without further purification. LCMS (m/z): 141 .0 [M+H]+; Rt = 0.18 min.
7.23 g	With sodium tetrahydroborate; ethanol at 20℃; for 4h;	1.2 Step 2: Preparation of 4-(ami nomethyl )tetrahydro-2//-pyran-4-carbonitrile (INT-3) To a solution of tetrahydro-4//-pyran-4,4-dicarbonitrile (INT-2, 9.0 g, 66.10 mmol) in EtOH (270 mL) was added NaB (7.50 g, 198.31 mmol) in portions. The reaction mixture was stirred at 20 °C for 4 hours, quenched by water (200 mL), and extracted with ethyl acetate (200 mL x 3). The combined organic phase was washed with brine (150 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to provide 4-(ami nomethyl )tetrahydro-2//- pyran-4-carbonitrile (INT-3, 7.23 g, 78% yield) as a brown oil. The crude product was used directly in the next step without further purification.

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - US2011/28492, 2011, A1 Location in patent: Page/Page column 25
[2]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2011/26904, 2011, A1 Location in patent: Page/Page column 63
[3]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2012/66065, 2012, A1 Location in patent: Page/Page column 81-82
[4]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2012/66070, 2012, A1 Location in patent: Page/Page column 89
[5]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2012/101063, 2012, A1 Location in patent: Page/Page column 118
[6]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2012/101065, 2012, A2 Location in patent: Page/Page column 85
[7]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2012/101066, 2012, A1 Location in patent: Page/Page column 75; 96
[8]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2012/101064, 2012, A1 Location in patent: Page/Page column 159
[9]Current Patent Assignee: ALGEN BIOTECHNOLOGIES - WO2021/231892, 2021, A1 Location in patent: Paragraph 0153; 0155-0156

3
[ 66256-28-8 ]
[ 111511-90-1 ]
4-(4-cyano-3-methylphenyl)tetrahydro-2H-pyran-4-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: 4-fluoro-1-iodo-2-methylbenzene With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: dihydro-2H-pyran-4,4(3H)-dicarbonitrile In tetrahydrofuran at 0 - 20℃; for 0.5h;

Reference： [1]Malapit, Christian A.; Luvaga, Irungu K.; Reeves, Jonathan T.; Volchkov, Ivan; Busacca, Carl A.; Howell, Amy R.; Senanayake, Chris H. [Journal of Organic Chemistry, 2017, vol. 82, # 9, p. 4993 - 4997]

4
[ 111511-90-1 ]
[ 1263374-32-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate In ethanol at 20℃; for 4h;	2 To a solution of dihydro-2H-pyran-4,4(3H)-dicarbonitrile (450 mg, 3.31 mmol in EtOH (15 mL) was added sodium borohydride (375 mg, 9.92 mmol) in portions and the mixture was stirred at room temperature for 4 hrs. The mixture was concentrated under reduced pressure and the residue was diluted with EtOAc (30 mL), washed with water (10 mL), dried over sodium sulfate, filtered off and concentrated under reduced pressure providing crude 4-(aminomethyl)tetrahydro-2H-pyran-4-carbonitrile (388mg), which was directly used in the next step without further purification. LCMS (m/z): 141.0[M+H]+; Rt = 0.18 min.

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2011/26917, 2011, A1 Location in patent: Page/Page column 64

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[ CAS No. 111511-90-1 ] {[proInfo.proName]}

Quality Control of [ 111511-90-1 ]

Related Doc. of [ 111511-90-1 ]

Product Details of [ 111511-90-1 ]

Safety of [ 111511-90-1 ]

Application In Synthesis of [ 111511-90-1 ]

[ 111511-90-1 ] Synthesis Path-Upstream 1~1

[ 111511-90-1 ] Synthesis Path-Downstream 1~4

Precautionary Statements-General

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