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[ CAS No. 130290-79-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 130290-79-8
Chemical Structure| 130290-79-8
Chemical Structure| 130290-79-8
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Product Details of [ 130290-79-8 ]

CAS No. :130290-79-8 MDL No. :MFCD02179435
Formula : C6H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :IPBPLHNLRKRLPJ-UHFFFAOYSA-N
M.W : 115.17 Pubchem ID :2773210
Synonyms :

Calculated chemistry of [ 130290-79-8 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 32.63
TPSA : 35.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : -0.12
Log Po/w (WLOGP) : 0.37
Log Po/w (MLOGP) : 0.21
Log Po/w (SILICOS-IT) : 1.04
Consensus Log Po/w : 0.63

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.41
Solubility : 44.6 mg/ml ; 0.387 mol/l
Class : Very soluble
Log S (Ali) : -0.17
Solubility : 78.4 mg/ml ; 0.681 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.77
Solubility : 19.6 mg/ml ; 0.171 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.42

Safety of [ 130290-79-8 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:2735
Hazard Statements:H227-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 130290-79-8 ]

* 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 [ 130290-79-8 ]
  • Downstream synthetic route of [ 130290-79-8 ]

[ 130290-79-8 ] Synthesis Path-Upstream   1~8

  • 1
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YieldReaction ConditionsOperation in experiment
85.3% With ammonia; hydrogen In methanol at 45 - 60℃; for 5 - 17 h; Example 43
(Synthesis of 4-aminomethyltetrahydropyran)
In an autoclave made of stainless equipped with a stirring device, a thermometer and a pressure gauge and having an inner volume of 200 ml were charged 10.0 g (90.0 mmol) of 4-cyanotetrahydropyran, 50.0 g of 22percent by weight ammonia-methanol solution and 2.0 g (17.0 mmol in terms of a nickel atom) of developed Raney nickel (available from Nikki Chemical Co., Ltd.; sponge nickel N154D), and the mixture was reacted under hydrogen atmosphere (0.51 to 0.61MPa) at 45 to 55°C for 17 hours under stirring.
After completion of the reaction, insoluble materials were filtered, and the filtrated material was washed with 30 ml of methanol.
The filtrate and the washed solution were combined and concentrated under reduced pressure, and then, the concentrate was distilled under reduced pressure (73 to 74°C, 2.67 kPa) to tive 7.94 g (Isolation yield; 76.6percent) of 4-aminomethyltetrahydropyran as colorless liquid.
Physical properties of the 4-aminomethyltetrahydropyran are as follows.
1H-NMR (DMSO-d6, δ (ppm)); 1.02 to 1.16 (2H, m), 1.10 to 1.50 (2H, brs), 1.34 to 1.45 (1H, m), 1.56 to 1.61 (2H, m), 2.39 (2H, d, J=6.3Hz), 3.20 to 3.29 (2H, m), 3.81 to 3.86 (2H, m)
CI-MS (m/e); 116 (M+1), 99
Example 45 (Synthesis of 4-aminomethyltetrahydropyran) In an autoclave made of stainless equipped with a stirring device, a thermometer and a pressure gauge and having an inner volume of 200 ml were charged 10.0 g (90.0 mmol) of 4-cyanotetrahydropyran, 100 ml of 22percent by weight ammonia methanol solution and 2.0 g (17.0 mmol in terms of a nickel atom) of developed Raney nickel (available from Nikki Chemical Co., Ltd.; sponge nickel N154D), and the mixture was reacted under hydrogen atmosphere (0.51 to 0.61MPa) at 50 to 60°C for 5 hours under stirring. After completion of the reaction, insoluble materials were filtered, the filtered material was washed with 30 ml of methanol, and the filtrate and the washed solution were combined. When this solution was analyzed by gas chromatography (Internal standard method), 8.84 g (Reaction yield: 85.3percent) of 4-aminomethyltetrahydropyran was found to be formed. Incidentally, bis(4-tetrahydropyranylmethyl)amine which is a by-product was not formed.
52.7% With hydrogen In methanol at 50 - 60℃; for 5 h; Comparative example 1 (Synthesis of 4-aminomethyltetrahydropyran) In an autoclave made of stainless equipped with a stirring device, a thermometer and a pressure gauge and having an inner volume of 200 ml were charged 10.0 g (90.0 mmol) of 4-cyanotetrahydropyran, 100 ml of methanol and 2.0 g (17.0 mmol in terms of a nickel atom) of developed Raney nickel (available from Nikki Chemical Co., Ltd.; sponge nickel N154D), and the mixture was reacted under hydrogen atmosphere (0.51 to 0.61 MPa) at 50 to 60°C for 5 hours under stirring. After completion of the reaction, insoluble materials were filtered, the filtered material was washed with 30 ml of methanol, and the filtrate and the washed solution were combined. When this solution was analyzed by gas chromatography (Internal standard method), 7.19 g (Reaction yield: 52.7percent) of the 4-aminomethyltetrahydropyran was found to be formed. Incidentally, 4.28 g of bis(4-tetrahydropyranylmethyl)amine which is a by-product was formed.
60 g With ammonia; hydrogen In methanol at 40 - 45℃; for 12 h; 4-Cyano-tetrahydropuran(500 mL) in methanolic ammonia (200 mL) was hydrogenated in the presence of Raney nickel (10 g) under a pressure of 4 to 5 kg/cm2 hydrogen gas for 12hours at 45 After cooling, the reaction solution was filtered through a Celite bed. The reaction mixture was distilled at 55 °C to provide the desired product (60 g, Yield: 0.60 w/w).
Reference: [1] Patent: EP1671937, 2006, A1, . Location in patent: Page/Page column 16-17
[2] Patent: EP1671937, 2006, A1, . Location in patent: Page/Page column 17
[3] Justus Liebigs Annalen der Chemie, 1938, vol. 535, p. 37,45
[4] Patent: US6372778, 2002, B1, . Location in patent: Example 80
[5] Patent: US2006/63804, 2006, A1, . Location in patent: Page/Page column 13
[6] Patent: EP1671937, 2006, A1, . Location in patent: Page/Page column 16-17
[7] Patent: WO2018/29711, 2018, A2, . Location in patent: Page/Page column 30
  • 2
  • [ 344329-76-6 ]
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Reference: [1] Patent: WO2004/58759, 2004, A1, . Location in patent: Page 284
[2] Patent: WO2005/66126, 2005, A1, . Location in patent: Page/Page column 88
[3] Patent: WO2007/75468, 2007, A1, . Location in patent: Page/Page column 111
  • 3
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Reference: [1] Patent: US5783701, 1998, A,
  • 4
  • [ 362703-30-8 ]
  • [ 130290-79-8 ]
Reference: [1] Patent: WO2018/29711, 2018, A2,
  • 5
  • [ 85064-61-5 ]
  • [ 130290-79-8 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1938, vol. 535, p. 37,45
  • 6
  • [ 125552-89-8 ]
  • [ 130290-79-8 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1938, vol. 535, p. 37,45
  • 7
  • [ 130290-79-8 ]
  • [ 406233-31-6 ]
  • [ 1228779-96-1 ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine In tetrahydrofuran at 20℃; for 5 h; 4-Fluoro-3-nitrobenzenesulfonamide (1.0 g, 4.54 mmol), (tetrahydro-2H-pyran-4-yl)methylamine (0.6 g, 4.49 mmol), Triethylamine (1.3 g, 6.81 mmol) was added to 10 ml of tetrahydrofuran solution. After stirring at room temperature for 5 h, the solvent was removed. Add 20ml of methanol to beat, After drying, the product was obtained in an amount of 1.4 g. The yield was 97percent.
94% With sodium carbonate In isopropyl alcohol at 55 - 65℃; for 4 h; In a 10-L reactor equipped with mechanical stirrer, thermometer and condenser, 4-fluoro-3-nitrobenzenesulfonamide (160 g, 0.73 mmol) was dissolved in 2-propanol (4.8 L) at 5-60°C. To this solution Na2CO3 (46.2 g, 0.44 mol, 0.6 equiv), 4-aminomethyltetrahydropyran (125.5 g, 1.09 mol, 1.5 equiv) were added and reaction mixture was stirred for 4 h at 55-65°C. The reaction mixture was diluted with water (4.8 L), cooled to 20-30°C and stirred overnight at 20-30°C. The slurry was filtered, the wet-cake was washed with water (5 x 0.8 L), and dried under vacuum at 90-95°C for 2 days to obtain desired compound (216.5 g, 94percent).
Reference: [1] Patent: CN108658983, 2018, A, . Location in patent: Paragraph 0116; 0117; 0118
[2] Patent: WO2017/156398, 2017, A1, . Location in patent: Paragraph 0322
[3] Patent: WO2010/65865, 2010, A2, . Location in patent: Page/Page column 226-227
[4] Patent: US2010/160322, 2010, A1, . Location in patent: Page/Page column 86
[5] Patent: US2010/305122, 2010, A1, . Location in patent: Page/Page column 118
[6] Patent: WO2011/150016, 2011, A1, . Location in patent: Page/Page column 82
[7] Patent: WO2012/71336, 2012, A1, . Location in patent: Page/Page column 9
[8] Patent: WO2016/24230, 2016, A1, . Location in patent: Paragraph 00738
  • 8
  • [ 130290-79-8 ]
  • [ 97-09-6 ]
  • [ 1228779-96-1 ]
YieldReaction ConditionsOperation in experiment
91% With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 12 h; To a 500 mL three-neck RB flask equipped with a mechanical stirrer were charged the 4-chloro-3-nitrobenzenesulfonamide, Compound M (10.0 g), diisopropylethylamine (17.5 g), (tetrahydro-2H-pyran-4-yl)methanamine (7.0 g) and acetonitrile (150 mL). The reaction mixture was adjusted to an internal temperature of 80° C. and agitated for no less than 12 hours. The product solution was cooled down to 40° C. and agitated for no less than 1 hour until precipitation observed. The product slurry was further cooled to 20° C. Water (75 mL) was slowly charged over no less than 1 hour, and the mixture cooled to 10° C. and agitated for no less than 2 hours before collected by filtration. The wet cake was washed with 1:1 mix of acetonitrile:water (40 mL). The wet cake was then reslurried in water (80 mL) at 40° C. for no less than 1 hour before collected by filtration. The wet cake was rinsed with water (20 mL), and dried at 75° C. under vacuum to give 12.7 g of the desired product in 99.9percent purity and in 91percent weight-adjusted yield. 1H NMR (DMSO-d6): δ 1.25 (m, 2H), 1.60 (m, 2H), 1.89 (m, 1H), 3.25 (m, 2H), 3.33 (m, 2H), 3.83 (m, 2H), 7.27 (d, J=9.3 Hz, 1H), 7.32 (s, NH2, 2H), 7.81 (dd, J=9.1, 2.3 Hz, 1H), 8.45 (d, J=2.2 Hz, 1H), 8.54 (t, J=5.9 Hz, 1H, NH).
60 g With N-ethyl-N,N-diisopropylamine In acetonitrile at 55 - 70℃; for 25 h; 4-chloro-3-nitrobenzene-1-sulfonamide (100 g), 4-cyano-tetrahydropyran(97.4 mL), and N,N- diisopropylethylamine (160 mL)were heated in acetonitrile to 70°C for 24 hours. After coolingto 55 °C,t he reaction mixture was distilled at 55 °C to remove s olvent until two reaction mass volumes remained. Water (800 mL) was added to the reaction and stirred 1 hour. The reaction mixture was filtered and the solid was washed with water (200 mL), followed by acetonitrile (300 mL) and ethyl acetate (300 mL). The solid was dried under vacuum at 55°C for 4 hours. (60g, Yield: 0.6w/w).
Reference: [1] Patent: US2014/275540, 2014, A1, . Location in patent: Paragraph 0149; 0150
[2] Patent: WO2018/29711, 2018, A2, . Location in patent: Page/Page column 31
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