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[ CAS No. 1116-98-9 ] {[proInfo.proName]}

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Chemical Structure| 1116-98-9
Chemical Structure| 1116-98-9
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Product Details of [ 1116-98-9 ]

CAS No. :1116-98-9 MDL No. :MFCD00001938
Formula : C7H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BFNYNEMRWHFIMR-UHFFFAOYSA-N
M.W : 141.17 Pubchem ID :70693
Synonyms :

Calculated chemistry of [ 1116-98-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.71
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.84
TPSA : 50.09 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.71
Log Po/w (XLOGP3) : 0.99
Log Po/w (WLOGP) : 1.24
Log Po/w (MLOGP) : 0.64
Log Po/w (SILICOS-IT) : 0.78
Consensus Log Po/w : 1.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.14
Solubility : 10.2 mg/ml ; 0.0723 mol/l
Class : Very soluble
Log S (Ali) : -1.63
Solubility : 3.31 mg/ml ; 0.0234 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.24
Solubility : 8.05 mg/ml ; 0.057 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.65

Safety of [ 1116-98-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1116-98-9 ]

* 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 [ 1116-98-9 ]
  • Downstream synthetic route of [ 1116-98-9 ]

[ 1116-98-9 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 40018-26-6 ]
  • [ 1116-98-9 ]
  • [ 59739-05-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 10, p. 1729 - 1740
[2] MedChemComm, 2014, vol. 5, # 2, p. 142 - 146
  • 2
  • [ 372-09-8 ]
  • [ 75-65-0 ]
  • [ 1116-98-9 ]
YieldReaction ConditionsOperation in experiment
86% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 5 h; Inert atmosphere Under argon, cyanoacetic acid (7.16 mmol) and t-butanol (6.51 mmol) are dissolved in anhydrous dichloromethane (30 mL) and cooled to 0° C. DCC (7.16 mmol) and DMAP (cat.) are added to the solution. The medium is stirred for 4 hours at 0° C. and 1 h at room temperature. The reaction mixture is filtered, then concentrated under reduced pressure. The thereby obtained is purified by column chromatography (SiO2, 20percent EtOAccyclohexane) in order to obtain the t-butyl ester as a colorless oil (86percent). [0501] 1H NMR (400 MHz, CDCl3): δ 4.23 (q, J=6.5 Hz, 2H, H-3), 3.44 (s, 2H, H-2), 1.28 (t, J=6.5 Hz, 3H, H-4).
84% With dicyclohexyl-carbodiimide In acetonitrile at 25℃; for 5 h; Cyanoacetic acid (1.705 g, 20 mmol) was dissolved in 20 mL acetonitrile. Tert-butyl alcohol (2.7 mL, 28 mmol) was added dropwise to the mixture under stirring at 25 °C. Then 24 mL of 1 M acetonitrile solution of DCC was added through a dropping funnel carefully. The reaction mixture was stirred for an additional 5 h and filtered through a sintered glass. Upon evaporation of the solvents, the reaction mixture was purified by flash column chromatography (silica gel, petroleum ether: ethyl acetate, 10:1) to afford the product (2.365 g, 84percent yield) as colourless oil. 1H-NMR (400 MHz, CDCl3) δ: 1.50 (s, 9H), 3.38 (s, 2H).
65% With 1,1'-carbonyldiimidazole In methanol; acetonitrile at 0℃; for 0.333333 h; (Z) -2- cyano-3-ethoxy-acrylate, t-butyl ester: cyanide acid containing 5 g (0.059 mole) and 5.2 g tertiary butyl alcohol (0.07 mmol, 1.2 equiv.) In acetonitrile / methanol (1: 1) was added portionwise at 0 12 g N, N'- dicyclohexyl carbodiimide (0.059 mole, 1 eq.) and stirred for 20 minutes, the reaction mixture was filtered, the organic layer was concentrated in a vacuum concentrator, after to give a yellow oil was purified by flash column chromatography on silica gel (petroleum ether / ethyl acetate = 10/1) to obtain 5.4 g of tert-butyl cyanoacetate (yield: 65percent). 200 ml of acetic anhydride was added to a solution containing 13.5 g of tert-butyl cyanoacetate (0.0957 mmol) in 17 g of triethoxymethane (0.115 mmol, 1.2 eq.), The reaction mixture was heated to reflux for fifteen hours, The solvent was removed in vacuo and then down a red oil (16 g, 85percent).
45% With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 18 h; t-Butanol (1.86 ml, 19.40 mmol, 1.1 eq) was mixed with cyanoacetic acid 7a (1.5 g, 17.63 mmol, 1 eq) in dry dichloromethane (30 ml). DCC (3.64 g, 17.63 mmol, 1 eq) was added dropwise. After stirring at room temperature for 18h, the white solid was filtrated and the resulting solution was concentrated in vacuo. Chromatography purification of the residue on silica gel with 9 cyclohexane/1 Ethyl acetate gave the desired ester 8k as a pale liquid (1.13 g, 45percent).

Reference: [1] Patent: US2015/38466, 2015, A1, . Location in patent: Paragraph 0500-0501
[2] Journal of Photochemistry and Photobiology A: Chemistry, 2013, vol. 272, p. 58 - 64
[3] Organic Letters, 2001, vol. 3, # 23, p. 3733 - 3735
[4] Journal of Organic Chemistry, 2002, vol. 67, # 25, p. 8975 - 8982
[5] Patent: TWI525093, 2016, B, . Location in patent: Page/Page column 182; 183; 184
[6] European Journal of Medicinal Chemistry, 2014, vol. 75, p. 391 - 402
[7] Journal of Medicinal Chemistry, 2017, vol. 60, # 3, p. 1076 - 1088
[8] Chemical and Pharmaceutical Bulletin, 1974, vol. 22, # 6, p. 1398 - 1404
[9] Tetrahedron, 2011, vol. 67, # 30, p. 5507 - 5515
[10] Patent: WO2011/114184, 2011, A1, . Location in patent: Page/Page column 50
[11] Applied Organometallic Chemistry, 2018, vol. 32, # 3,
  • 3
  • [ 5292-43-3 ]
  • [ 151-50-8 ]
  • [ 1116-98-9 ]
Reference: [1] Journal of the American Chemical Society, 1942, vol. 64, p. 2274
  • 4
  • [ 372-09-8 ]
  • [ 115-11-7 ]
  • [ 1116-98-9 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1974, p. 2985 - 2986
  • 5
  • [ 107-59-5 ]
  • [ 151-50-8 ]
  • [ 1116-98-9 ]
Reference: [1] Helvetica Chimica Acta, 1959, vol. 42, p. 1214,1220
  • 6
  • [ 107-59-5 ]
  • [ 151-50-8 ]
  • [ 1116-98-9 ]
  • [ 106271-05-0 ]
Reference: [1] Helvetica Chimica Acta, 1959, vol. 42, p. 1214,1220
  • 7
  • [ 16130-58-8 ]
  • [ 75-65-0 ]
  • [ 1116-98-9 ]
Reference: [1] Journal of the Chemical Society, 1955, p. 423,428, 429
  • 8
  • [ 5292-43-3 ]
  • [ 13435-20-6 ]
  • [ 1116-98-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1978, p. 1946 - 1962
  • 9
  • [ 1116-98-9 ]
  • [ 82102-37-2 ]
  • [ 460-00-4 ]
  • [ 4640-67-9 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 4, p. 1358 - 1366
  • 10
  • [ 1116-98-9 ]
  • [ 15231-41-1 ]
YieldReaction ConditionsOperation in experiment
198 g With ammonia; hydrogen In methanol at 55℃; for 6 h; Sealed tube The reaction vessel was charged with 200g of tert-butyl cyanoacetate was added 1kg2percent methanol - ammonia solution, 20g Raney nickel was added, the reaction vessel sealed, purged with nitrogen three times, purged with hydrogen three times. Charged with hydrogen pressure 5Mpa, heated to 55 , the reaction was stirred 6h, midway continuous supply of hydrogen.After completion of the reaction, the catalyst was removed by filtration, the filtrate was concentrated to 200g of ethyl acetate was added, under cooling, was added ethyl acetate - hydrogen chloride to pH 3, the system was concentrated, the precipitated solid was dried. To give the product 198g.
Reference: [1] Patent: CN105367435, 2016, A, . Location in patent: Paragraph 0022; 0023
  • 11
  • [ 1116-98-9 ]
  • [ 2719-27-9 ]
  • [ 62455-70-3 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 5, p. 1137 - 1143
  • 12
  • [ 1116-98-9 ]
  • [ 462100-44-3 ]
  • [ 130892-40-9 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 35, p. 8423 - 8442
  • 13
  • [ 1116-98-9 ]
  • [ 32779-36-5 ]
  • [ 831203-15-7 ]
YieldReaction ConditionsOperation in experiment
45%
Stage #1: With sodium hydride In dimethyl sulfoxide at 20℃; for 1 h; Inert atmosphere
Stage #2: at 20℃; for 8 h; Inert atmosphere
Stage #3: With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 16 h;
To a suspension of sodium hydride (53 mg (60percent oil suspension), 1.34 mmol) in DMSO (2 ml) at room temperature under a nitrogen atmosphere was added tert-butyl cyanoacetate (197 mg, 39 mmol) in DMSO (1 ml) was added dropwise over 15 minutes and then stirred at room temperature for 1 hour.5-Bromo-2-chloropyrimidine (100 mg, 0.52 mmol) was added to the reaction solution, and the mixture was stirred at room temperature for 8 hours. Next, a saturated aqueous solution of ammonium chloride was added to the reaction system, extracted with ethyl acetate, washed with water, and then concentrated under reduced pressure to obtain a crude product.Subsequently, trifluoroacetic acid (1.8 ml) was added to a solution of the dried crude product in dichloromethane (2.3 ml) at 0 ° C., and the mixture was stirred for 1 hour and then allowed to warm to room temperature and stirred for 15 hours did.The reaction solution was neutralized with a saturated aqueous sodium hydrogen carbonate solution, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was filtered and concentrated under reduced pressure to obtain a crude product of (5-bromopyrimidin-2-yl) acetonitrile.The obtained crude product was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to obtain (5-bromopyrimidin-2-yl) acetonitrile. Yield 46 mg, yield 45percent, white solid.
Reference: [1] Patent: JP2017/178911, 2017, A, . Location in patent: Paragraph 0152; 0153
  • 14
  • [ 624-28-2 ]
  • [ 1116-98-9 ]
  • [ 831203-34-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 20, p. 6558 - 6562
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