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[ CAS No. 1306763-57-4 ] {[proInfo.proName]}

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Chemical Structure| 1306763-57-4
Chemical Structure| 1306763-57-4
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Product Details of [ 1306763-57-4 ]

CAS No. :1306763-57-4 MDL No. :MFCD16295046
Formula : C10H11ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :NYCLSOKJNLLCHQ-PPHPATTJSA-N
M.W : 194.66 Pubchem ID :53350322
Synonyms :

Calculated chemistry of [ 1306763-57-4 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 53.45
TPSA : 49.81 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.73
Log Po/w (WLOGP) : 1.98
Log Po/w (MLOGP) : 1.37
Log Po/w (SILICOS-IT) : 1.9
Consensus Log Po/w : 1.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.48
Solubility : 0.647 mg/ml ; 0.00332 mol/l
Class : Soluble
Log S (Ali) : -2.39
Solubility : 0.789 mg/ml ; 0.00405 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.71
Solubility : 0.379 mg/ml ; 0.00195 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.19

Safety of [ 1306763-57-4 ]

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

Application In Synthesis of [ 1306763-57-4 ]

* 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 [ 1306763-57-4 ]

[ 1306763-57-4 ] Synthesis Path-Downstream   1~14

YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In 1,4-dioxane; at 20℃; for 1.5h; General procedure: To crude (R)-N-((R)-4-cyano-2,3 -dihydro-JH-inden- l-yl)-2-methylpropane-2-sulfinamide INT-5 (52.9 g, 0.20 mol) in MeOH (200 mL) was added4N HC1 in dioxane (152.0 mL, 0.60 mol) and the resulting yellow suspension was stirred at room temperature for 1.5 h. The crude reaction mixture was diluted with MeOH (500 mL) and filtered to remove some Ti by-products. The filtrate was concentrated and the resulting solid refluxed in acetonitrile (500 mL). The resultingwhite solid was collected to produce 13.0 g (31% over 3 steps) of the HC1 salt of (R)-1- amino-2, 3 -dihydro-JH-indene- 1 -yl)-4-carbonitrile INT-6. LCMS-ESI (m/z) calculated for C,0H,0N2: 158.2; found 142.0 [M-NH2], tR = 0.84 mm. ?H NMR (400 MHz, DMSO) 8.61 (s, 3H), 7.96 (d, J= 7.7, 1H), 7.83 (d, J 7.5, 1H), 7.52 (t, J 7.7, 1H), 4.80 (s, 1H), 3.23 (ddd, J= 16.6, 8.7, 5.2, 1H), 3.05 (ddd, J= 16.6, 8.6, 6.3, 1H), 2.62 -2.51 (m, 1H), 2.15 - 2.01 (m, 1H). ?3C NIVIR (101 IVIHz, DMSO) 148.09, 141.15,132.48, 130.32, 127.89, 117.27, 108.05, 54.36, 39.08, 29.64. The free base can beprepared by extraction with iN NaHCO3 and DCM. LCMS-ESI (m/z) calculated forC,0H,0N2: 158.2; found 142.0 [M-NH2], tR = 0.83 mm. ?H NIVIR (400 MHz, CDC13)7.52-7.38 (m, 2H), 7.23 (dd, J= 17.4, 9.8, 1H), 4.35 (t, J= 7.6, 1H), 3.11 (ddd, J=16.8, 8.7, 3.2, 1H), 2.89 (dt, J= 16.9, 8.5, 1H), 2.53 (dddd, J= 12.8, 8.1, 7.3, 3.2, 1H),1.70 (dtd, J = 12.8, 8.8, 8.0, 1H). ?3C NIVIR (101 MHz, DMSO) 150.16, 146.67,130.19, 128.74, 127.38, 117.77, 107.42, 56.86, 38.86, 29.14. Chiral HPLC: (R)-1- amino-2, 3 -dihydro-JH-indene- 1 -yl)-4-carbonitrile was eluted using 5% EtOH in hexanes, plus 0.05% TEA: 95% ee, tR = 23.02 mm. The (S)-enantiomer INT-7 wasprepared in an analogous fashion using ()-2-methylpropane-2-sulfinamide. tR for (5)- enantiomer= 20.17 mm.
  • 2
  • (1S)-1-[(1S)-1-(4-methoxyphenyl)ethyl]amino}-2,3-dihydro-1H-indene-4-carbonitrile p-toluenesulfonic acid salt [ No CAS ]
  • [ 1306763-57-4 ]
  • 3
  • (1S)-1-[(1S)-1-(4-methoxyphenyl)ethyl]amino}-2,3-dihydro-1H-indene-4-carbonitrile [ No CAS ]
  • [ 1306763-57-4 ]
YieldReaction ConditionsOperation in experiment
81.35% 48.0 gm of amine (Formula 16) was added to 288.0 of trifluoroacetic acid at ambient temperature and heated the reaction mass to 70-75C. The reaction mass was refluxed for 16.0 hr. After completion, TFA was distilled out under vacuum at 40- 50C and cooled to 25-30C. The residue was diluted with water and washed with toluene. The aqueous layer was basified with sodium hydroxide solution and the product was extracted with ethyl acetate. The organic layer was washed with brine and concentrated under vacuum at 40-45C to get crude amine. The amine was diluted with 240ml of ethyl acetate and stirred. 48 ml of IPA-HCl (-13%) was added and stirred for l.Ohr. The product was filtered, washed with ethyl acetate and dried to obtain off-white solid of compound of Formula 6 (26.0 gm, 81.35% yield) with HPLC Purity 98.27%, Chiral HPLC Purity (S) 100.0% & SOR -45 (c=l in Methanol at 25C).MR: Not melted up to 270C; IR (KBr, cm-1): 2229, 1497, 1370, 1127; 1H- NMR (DMSO-d6): delta 8.91 (br, 3H), 8.07-8.05 (d, 1H, J=7.68Hz), 7.81-7.79 (d, 1H, J=7.63Hz), 7.51-7.47 (t, 1H, J=7.71Hz), 4.80-4.77 (t, 1H, J=6.27Hz), 3.24-3.20 (m, 1H), 3.07-3.01 (m, 1H), 2.56-2.53 (m, 1H), 2.16-2.12(m, 1H);13C-NMR (DMSO- d6): 148.59, 141.64, 132.96, 130.86, 128.36, 117.77, 108.53, 54.87, 39.96, 30.14; MS (m/z): 159.0 [M+l]+, 142.0 [M-NH2].
  • 4
  • [ 1306763-57-4 ]
  • (S)-tert-butyl 2-(tert-butyldimethylsilyloxy)ethyl-(4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate [ No CAS ]
  • 5
  • [ 1306763-57-4 ]
  • (S)-tert-butyl 2-(tert-butyldimethylsilyloxy)ethyl-(4-(N-hydroxycarbamimidoyl)-2,3-dihydro-1H-inden-1-yl)carbamate [ No CAS ]
  • 6
  • [ 1306763-57-4 ]
  • tert-butyl(1S)-4-[5-[3-cyano-4-(propan-2-yloxy)phenyl]-1,2,4-oxadiazol-3-yl]-2,3-dihydro-1H-inden-1-yl-N-[2-[(tert-butyldimethylsilyl)oxy]ethyl]carbamate [ No CAS ]
  • C28H32N4O5 [ No CAS ]
  • 7
  • [ 1306763-57-4 ]
  • 5-{3-[(1S)-1-[(2-hydroxyethyl)amino]-2,3-dihydro-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl}-2-(propan-2-yloxy)benzonitrile hydrochloride [ No CAS ]
  • 8
  • [ 1306763-57-4 ]
  • 5-[3-[(1S)-1-[(2-hydroxyethyl)amino]-2,3-dihydro-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(propan-2-yloxy)benzonitrile [ No CAS ]
  • 9
  • [ 24424-99-5 ]
  • [ 1306763-57-4 ]
  • [ 1306763-31-4 ]
YieldReaction ConditionsOperation in experiment
92.71% With triethylamine; In dichloromethane; at 5 - 20℃; for 2h; To a stirred solution of 30.0 gm of amine.HCl (Formula 6) (0.154 moles) and 300.0 of dichloromethane, 31.2 gm of triethyl amine (0.308 moles, 2.0 eq.)was added at 5-15C. 43.47 gm of Boc anhydride (85%) (0.169 moles, 1.1 eq.) was added and warmed to ambient temperature. The reaction mass was stirred for 2.0hrs. After completion, the reaction mass was washed with water and brine solution. The organic layer was concentrated, cooled and stirred with hexane. The product was filtered, washed with hexane and dried to obtain off-white solid of Formula 7(36.9 gm, 92.71% yield) with HPLC Purity 96.93% & SOR -122 (c=l in CHC13at 25C).MR: 129.7-132.1C; IR (KBr, cm"1): 3364, 2979, 2225, 1677, 1514, 1169; 1H- NMR(CDC13): delta 7.56-7.50 (m, 2H), 7.33-7.29 (t, 1H, J=7.64Hz), 5.25-5.23 (m, 1H), 4.76-4.74 (d, 1H, J=6.24Hz) , 3.20-3.14 (m, 1H), 2.99 (m, 1H), 2.68-2.64 (m, 1H), 1.89-1.83 (m, 1H), 1.49 (s, 9H);13C-NMR(CDC13): 155.55, 147.03, 145.44, 131.34, 128.72, 127.56, 117.50, 109.01, 79.84, 55.79, 33.51, 29.62, 28.37(3C); MS (m/z): 259.0 [M+l]+, 203.1 [M-C(CH3)3]+.
  • 10
  • [ 60899-34-5 ]
  • [ 1306763-57-4 ]
  • 11
  • 1-[(1S)-1-(4-methoxyphenyl)ethyl]imino}-2,3-dihydro-1H-indene-4-carbonitrile [ No CAS ]
  • [ 1306763-57-4 ]
  • 12
  • [ 1306763-57-4 ]
  • [ 627-11-2 ]
  • C13H13ClN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; at 0 - 5℃; for 1h; 2g of (S)-l-amino-2,3-dihydro-lH-indene-4-carbonitrile hydrochloride were suspended in 15 ml of tetrahydrofurane (THF). 3.15 ml of triethylamine were added. The mixture was cooled to 0-5C. 1.27 ml of 2-Chloroethyl chloroformate was added drop-wise to the mixture. The mixture was stirred at a temperature between 0 - 5C for additional one hour to obtain a suspension. The suspension was filtered and the filtration cake was washed with 4 ml THF. Combined filtrates were cooled to 0-5C and 4 ml of 25% in methanol solution of sodium methanolate were added. The mixture was stirred at 0-5C for 1.5 hours. Then it was warmed to 20-25C and concentrated under vacuum. The residue was diluted with 10 ml of water and 15 ml of ethylacetate (EtOAc). The phases were separated and the water phase was extracted with additional 15 ml of EtOAc. Combined organic extracts were dried over MgS04 and evaporated to dryness to give 1.99 g of (S)-l-(2-oxooxazolidin-3-yl)-2,3-dihydro-lH-indene- 4-carbonitrile (85% of the theoretical yield, purity HPLC IN 97.7%). The structure of (S)-l- (2-oxooxazolidin-3-yl)-2,3-dihydro-lH-indene-4-carbonitrile was confirmed by NMR.
  • 13
  • [ 1306763-57-4 ]
  • [ 627-11-2 ]
  • (S)-N-hydroxy-1-(2-oxooxazolidin-3-yl)-2,3-dihydro-1H-indene-4-carboximidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% 35 g of (S)-l-amino-2,3-dihydro-lH-indene-4-carbonitrile hydrochloride was mixed with 245 ml of 2-Methyltetrahydrofurane. Tot the mixture a solution of 52.4 g of potassium carbonate in 105 ml of water was added in one portion with stirring to obtain two phase mixture. The temperature of the mixture was set to 15C and 22.27 ml of 2-chloroethyl carbonochloridate was added. Temperature of the mixture was maintained below 35C during the addition. The temperature of the mixture was set to 22C and the mixture was stirred for additional 30 minutes. Then temperature of the mixture was set to 70C and the mixture was stirred to obtain a solution. The phases were separated at a temperature 60-70C. Then 105 ml of 5M potassium hydroxide water solution was added in one portion, followed by addition of 1.75 g of tetrabutylammonium chloride. The two phase mixture was then vigorously stirred for 1 hour. The phases were separated while keeping the temperature of the mixture between 50-70C. Organic phase was washed with 60 ml of water. 105 ml of isopropanol was added followed by 16.5 ml 50% water solution of hydroxy lamine. The mixture was stirred for 24 hours at 65C, then cooled to 0-5C and filtered. The filtration cake was washed with 2x50 ml of isopropanol and the product was dried at 45C in vacuum overnight to give (S)- (0110) N-hydroxy-l-(2-oxooxazolidin-3-yl)-2,3-dihydro-lH-indene-4-carboximidamide in yield 91% and 99.4% purity (HPLC IN).
  • 14
  • [ 1306763-31-4 ]
  • [ 1306763-57-4 ]
YieldReaction ConditionsOperation in experiment
91% With hydrogenchloride; In methanol; isopropyl alcohol; at 45℃; for 3h; 29.8 g oftert-Butyl (S)-(4-cyano-2,3-dihydro-lH-inden-l-yl)carbamate was suspended in 210 ml of MeOH followed by addition of 90 ml of 5 mol/1 HCI solution in isopropanol. The reaction mixture was stirred at 45 C for 3 h. The reaction mixture was concentrated to approximately 150 ml and transferred to 100 ml of methyl tert-butyl ether. The suspension was cooled to (0 to -5) C and stirred for 20 minutes. The suspension was filtered, the filtration cake was washed with 2x50 ml of cold methyl tert-butyl ether. The obtained material was dried at room temperature (20-25C) to give 20.5 g of the title compound (yield 91 %, HPLC purity 99.8 %).
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[ 1306763-57-4 ]

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[ 196929-78-9 ]

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