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[ CAS No. 496807-97-7 ] {[proInfo.proName]}

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Chemical Structure| 496807-97-7
Chemical Structure| 496807-97-7
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Quality Control of [ 496807-97-7 ]

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Product Details of [ 496807-97-7 ]

CAS No. :496807-97-7 MDL No. :MFCD03452800
Formula : C5H10ClF2N Boiling Point : No data available
Linear Structure Formula :- InChI Key :LEHHIPIDKQVNEV-UHFFFAOYSA-N
M.W : 157.59 Pubchem ID :2758349
Synonyms :

Calculated chemistry of [ 496807-97-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 37.86
TPSA : 12.03 ?2

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) : -6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.76
Log Po/w (WLOGP) : 2.27
Log Po/w (MLOGP) : 1.49
Log Po/w (SILICOS-IT) : 1.98
Consensus Log Po/w : 1.5

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.93
Solubility : 1.87 mg/ml ; 0.0119 mol/l
Class : Very soluble
Log S (Ali) : -1.63
Solubility : 3.69 mg/ml ; 0.0234 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.82
Solubility : 2.39 mg/ml ; 0.0152 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.41

Safety of [ 496807-97-7 ]

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

Application In Synthesis of [ 496807-97-7 ]

* 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 [ 496807-97-7 ]

[ 496807-97-7 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 741288-41-5 ]
  • [ 496807-97-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; hydrogen;5% palladium-on-charcoal; In methanol; ethanol; for 22h; To a solution of 1-benzyl-piperidin-3-one (1G) in CH2CI2 (LOML) is added [bis (2-methoxy- ethyl) amino] SULFER TRIFLUORIDE (1. 84mL) at 0C, and stirred for 1.5hr at room temperature. The reaction mixture is poured in aqueous NaHC03 and extracted with ethyl acetate. The organic layer is successively washed with H20 and aqueous NACI, dried over MgS04, and concentrated in vacuo. The residue is purified by column chromatography to give a colorless oil. The oil and Pd/C (5% w/w on activated carbon, 100MG) in HCI in ETOH/MEOH (50mL) is stirred for 22hr under H2 atmosphere. The reaction mixture is filtrated through celite pad. 4The filtrate is added HCI in EtOAc, then concentrated in vacuo to provide the title compound.
  • 2
  • E-4-(2-chloro-acetylamino)-adamantane-1-carboxylic acid methyl ester [ No CAS ]
  • [ 496807-97-7 ]
  • E-4-[2-(3,3-difluoro-piperidin-1-yl)-acetylamino]-adamantane-1-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
A solution of E-4-(2-chloro-acetylamino)-adamantane-1-carboxylic acid methyl ester (0.075 g, 0.26 mmoles) from Example 25B, in MeOH (1.5 mL) and DIPEA (0.05 mL, 0.29 mmoles) was treated with <strong>[496807-97-7]3,3-difluoro-piperidine hydrochloride</strong> (0.062 g, 0.39 mmoles) and stirred for 2 hours at 80 C. The cooled reaction mixture was purified on reverse phase HPLC and hydrolyzed with 3N HCl at 60 C. over 6 hours. Drying of the reaction mixture under reduced pressure provided the hydrochloride salt of the title compound as a white solid (50 mg, 52%). 1H NMR (300 MHz, DMSO-d6) delta 8.45 (m, 1H), 3.97 (bs, 2H), 3.88 (m, 1H), 3.65 (m, 2H), 3.23 (m, 2H), 2.11 (m, 2H), 1.91 (m, 11H), 1.79 (m, 2H), 1.47 (m, 2H); MS (DCI+) m/z 357 (M+H)+.
  • 3
  • E-4-(2-bromo-propionylamino)-adamantane-1-carboxylic acid amide [ No CAS ]
  • [ 496807-97-7 ]
  • E-4-[2-(3,3-difluoropiperidine-1-yl)-propionylamino]-adamantane-1-carboxylic acid amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With N-ethyl-N,N-diisopropylamine; In methanol; at 70℃; A solution of E-4-(2-bromo-propionylamino)-adamantane-1-carboxylic acid amide (33 mg, 0.1 mmoles) and the hydrochloride of 3,3-difluoropiperidine (19 mg, 0.12 mmol) from Example 31B in MeOH (0.5 mL) and DIPEA (0.1 mL) was stirred overnight at 70 C. The MeOH was removed under reduced pressure and the residue purified on reverse phase HPLC to provide the title compound as a white solid (18 mg, 48%). 1H NMR (400 MHz, Py-d5) delta 7.92 (d, J=7.7 Hz, 1H), 7.51 (s, 2H), 4.32 (d, J=7.7 Hz, 1H), 3.42 (q, J=7 Hz, 1H), 2.92 (q, J=10.7 Hz, 1H), 2.78 (q, J=11.6 Hz, 1H), 2.5 (m, 2H), 2.27-2.10 (m, 8H), 1.98-1.88 (m, 5H), 1.68 (m, 2H), 1.55 (m, 2H), 1.32 (d, 3H); MS (ESI+) m/z 370 (M+H)+.
  • 4
  • [ 496807-97-7 ]
  • (E)-4-(2-bromo-propionylamino)-adamantane-1-carboxamide [ No CAS ]
  • (E)-4-[2-(3,3-difluoropiperidine-1-yl)-propionylamino]-adamantane-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In methanol; at 70℃; A solution of (E)-4-(2-bromo-propionylamino)-adamantane-1-carboxamide (33 mg, 0.1 mmoles) and the hydrochloride of 3,3-difluoropiperidine (19 mg, 0.12 mmol) from Example 31B in MeOH (0.5 mL) and DIPEA (0.1 mL) was stirred overnight at 70 C. The MeOH was removed under reduced pressure and the residue purified on reverse phase HPLC to provide the title compound as a white solid. 1H NMR (400 MHz, Py-d5) delta 7.92 (d, J=7.7 Hz, 11H), 7.51 (s, 2H), 4.32 (d, J=7.7 Hz, 1H), 3.42 (q, J=7 Hz, 1H), 2.92 (q, J=10.7 Hz, 1H), 2.78 (q, J=11.6 Hz, 1H), 2.5 (m, 2H), 2.27-2.10 (m, 8H), 1.98-1.88 (m, 5H), 1.68 (m, 2H), 1.55 (m, 2H), 1.32 (d, 3H); MS(ESI+) m/z 370 (M+H)+.
  • 5
  • [ 496807-97-7 ]
  • [ 933796-13-5 ]
  • 8-[(3,3-difluoropiperidin-1-yl)methyl]-3-(phenylsulfonyl)quinoline hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% Example 27; 8-[(3,3-Difluoropiperidin-1-yl)methyl]-3-(phenylsulfonyl)quinoline hydrochloride(E27); A suspension of 3-(phenylsulfonyl)quinoline-8-carbaldehyde (D3) (45 mg, 0.15 mmol) in anhydrous dichloromethane (1 ml) was treated with <strong>[496807-97-7]3,3-difluoropiperidine hydrochloride</strong> (26 mg, 0.165 mmol) and sodium triacetoxyborohydride (37 mg, 0.175 mmol) and the mixture was stirred under argon at room temperature for 18h. The reaction mixture was then diluted with dichloromethane (30 ml) and washed with aqueous sodium bicarbonate solution (2 x 20ml). The dichloromethane solution was dried by filtration through a hydrophobic cartridge and evaporated to a gum. This material was dissolved in a mixture of dimethylsulphoxide (0.45 ml) and acetonitrile (0.45 ml) and purified by mass-directed auto-preparative chromatography using a 10 minute gradient containing water and between 15% and 55% acetonitrile with 0.1% formic acid. Product fractions were collected and evaporated to a gum. This material was dissolved in ether (2 ml) and treated with 1M hydrogen chloride in ether (1 ml). The mixture was evaporated, dissolved in ether and re-evaporated to yield the title compound as a white solid (35 mg, 0.08 mmol, 53%). deltaH (CD3OD, 400MHz) 1.90-2.40 (4H, m), 3.20-3.90 (4H, m), 5.06 (2H, s), 7.61-7.72 (3H, m), 7.86 (IH, t, J = 7Hz), 8.06-8.16 (3H, m), 8.34 (1 H, dd, J = 1.2, 8.4Hz), 9.17 (1 H, d, J = 2Hz), 9.40 (1 H, d, J = 2Hz). Mass spectrum: C2IH20F2N2O2S requires 402; found 403 (MH+)
  • 6
  • [ 496807-97-7 ]
  • [ 933796-19-1 ]
  • 8-[1-(3,3-difluoro-1-piperidinyl)ethyl]-3-(phenylsulfonyl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
11% Example 37; 8-[1 -(3,3-Dif luoro-1 -piperidinyl)ethyl]-3-(phenylsulfonyl)quinoline (E37); A suspension of 1-[3-(phenylsulfonyl)quinolin-8-yl]ethanone (D8) (96 mg, 0.3 mmol) in anhydrous dichloromethane (2 ml) was treated with <strong>[496807-97-7]3,3-difluoropiperidine hydrochloride</strong> (52 mg, 0.33 mmol) and sodium triacetoxyborohydride (95 mg, 0.44 mmol) and the mixture was stirred under argon at room temperature for 3 days. The reaction mixture was then diluted with dichloromethane (75 ml) and washed with aqueous sodium bicarbonate solution (2 x 50ml). The dichloromethane solution was dried by filtration through a hydrophobic cartridge and evaporated to a gum. This material was dissolved in a mixture of dimethylsulphoxide (0.90 ml) and acetonitrile (0.90 ml) and purified by mass- directed auto-preparative chromatography using a 10 minute gradient containing water EPO <DP n="52"/>and between 15% and 55% acetonitrile with 0.1% formic acid. Product fractions were collected and evaporated to give the title compound as a colourless foam (14 mg, 11%). deltaH (CDCI3, 400MHz) 1.41 (3H, t, J = 7Hz), 1.70-1.89 (4H, m), 2.33-2.36 (1 H, m), 2.61- 2.78 (3H, m), 5.00 (1 H, q, J = 7Hz), 7.52-7.63 (3H, m), 7.70 (1 H, t, J = 8Hz), 7.86 (1 H, dd, J = 1.2Hz, 7Hz), 7.99-8.10 (3H, m), 8.81 (1 H, d, J = 2Hz), 9.24 (1 H1 d, J = 2Hz) Mass spectrum: C22H22F2N2O2S requires 416; found 417 (MH+)
11% With sodium tris(acetoxy)borohydride; In dichloromethane; at 20℃; for 72h; A suspension of l-[3-(phenylsulfonyl)quinolin-8-yl]ethanone (96 mg, 0.3 mmol) in anhydrous dichloromethane (2 ml) was treated with <strong>[496807-97-7]3,3-difluoropiperidine hydrochloride</strong> (52 mg, 0.33 mmol) and sodium triacetoxyborohydride (95 mg, 0.44 mmol) and the mixture was stirred under argon at room temperature for 3 days. The reaction mixture was then diluted with dichloromethane (75 ml) and washed with aqueous sodium bicarbonate solution (2 x 50ml). The dichloromethane solution was dried by filtration through a hydrophobic cartridge and evaporated to a gum. This material was dissolved in a mixture of dimethylsulphoxide (0.90 ml) and acetonitrile (0.90 ml) and purified by mass-directed auto -preparative chromatography using a 10 minute gradient containing water and between 15% and 55% acetonitrile with 0.1% formic acid. Product fractions were collected and evaporated to give the title compound as a colourless foam (14 mg, 11%). <n="211"/>deltaH (CDCl3, 400MHz) 1.41 (3H, t, J = 7Hz), 1.70-1.89 (4H, m), 2.33-2.36 (IH, m), 2.61-2.78 (3H, m), 5.00 (IH, q, J = 7Hz), 7.52-7.63 (3H, m), 7.70 (IH, t, J = 8Hz), 7.86 (IH, dd, J = 1.2Hz, 7Hz), 7.99-8.10 (3H, m), 8.81 (IH, d, J = 2Hz), 9.24 (IH, d, J = 2Hz) Mass spectrum: C22H22F2N2O2S requires 416; found 417 (MH+)
  • 7
  • [ 496807-97-7 ]
  • [ 933796-27-1 ]
  • [ 933796-28-2 ]
YieldReaction ConditionsOperation in experiment
Description 20; 8-[(3,3-Dif luoro-1 -piperidinyl)methyl]-3-iodoquinoline (D20); 3-lodo-delta-quinolinecarbaldehyde (D19) (2g, 7.06mmol) and <strong>[496807-97-7]3,3-difluoropiperidine hydrochloride</strong> (0.94g, 7.77mmol) were dissolved in dichloromethane (20ml). Sodium triacetoxyborohydride (2.25g, 10.6mmol) and acetic acid (0.44ml, 7.77mmol) were added and the reaction stirred at room temperature under argon overnight. The reaction was diluted with dichloromethane, cooled and basified with saturated sodium bicarbonate solution. The organics were dried over sodium sulfate, filtered and concentrated in vacuo to yield a brown oil (2.89g). The residue was purified on the Jones Flashmaster Il with an IST SPE 7Og silica column eluting a gradient of 5-12% ethyl acetate/n-hexane over 40 minutes. This yielded the title compound as a pale yellow oil (2.27g).LC/MS [MH+] 389 consistent with molecular formula C15H15F2IN2.
With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃; 3-Iodo-8-quinolinecarbaldehyde (2g, 7.06mmol) and <strong>[496807-97-7]3,3-difluoropiperidine hydrochloride</strong> (0.94g, 7.77mmol) were dissolved in dichloromethane (20ml). Sodium triacetoxyborohydride (2.25g, 10.6mmol) and acetic acid (0.44ml, 7.77mmol) were added and the reaction stirred at room temperature under argon overnight. The reaction was diluted with dichloromethane, cooled and basified with saturated sodium bicarbonate solution. The organics were dried over sodium sulfate, filtered and concentrated in vacuo to yield a brown oil (2.89g). The residue was purified on the Jones Flashmaster II with an 1ST SPE 7Og silica column eluting a gradient of 5-12% ethyl acetate/?-hexane over 40 minutes. This yielded the title compound as a pale yellow oil (1.2Ig).LC/MS [MH+] 389 consistent with molecular formula Ci5H15F2IN2.
  • 8
  • [ 496807-97-7 ]
  • [ 933796-13-5 ]
  • [ 933825-16-2 ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; In dichloromethane; at 20℃; for 18h; A suspension of 3-(phenylsulfonyl)quinoline-8-carbaldehyde (45 mg, 0.15 mmol) in anhydrous dichloromethane (1 ml) was treated with <strong>[496807-97-7]3,3-difluoropiperidine hydrochloride</strong> (26 mg, 0.165 mmol) and sodium triacetoxyborohydride (37 mg, 0.175 mmol) and the mixture was stirred under argon at room temperature for 18h. The reaction mixture was then diluted with dichloromethane (30 ml) and washed with aqueous sodium bicarbonate solution (2 x 20ml). The dichloromethane solution was dried by filtration through a hydrophobic cartridge and evaporated to a gum. This material was dissolved in a mixture of dimethylsulphoxide (0.45 ml) and acetonitrile (0.45 ml) and purified by mass-directed auto -preparative chromatography using a 10 minute gradient containing water and between 15% and 55% acetonitrile with 0.1% formic acid. Product fractions were collected and evaporated to a gum. This material was dissolved in ether (2 ml) and treated with IM hydrogen chloride in ether (1 ml). The mixture was evaporated, dissolved in ether and re-evaporated to yield the title compound as a white solid (35 mg, 0.08 mmol, 53%). <n="206"/>deltaH (CD3OD, 400MHz) 1.90-2.40 (4H, m), 3.20-3.90 (4H, m), 5.06 (2H, s), 7.61-7.72 (3H, m), 7.86 (IH, t, J = 7Hz), 8.06-8.16 (3H, m), 8.34 (IH, dd, J = 1.2, 8.4Hz), 9.17 (IH, d, J = 2Hz), 9.40 (IH, d, J = 2Hz). Mass spectrum: C2IH20F2N2O2S requires 402; found 403 (MH+)
  • 9
  • [ 496807-97-7 ]
  • [ 1111184-08-7 ]
  • [ 1111184-15-6 ]
YieldReaction ConditionsOperation in experiment
86% With triethylamine; In dichloromethane; at 20℃; for 2h; Intermediate 7; 6-[(3,3-Difluoro-1 -piperidinyl)sulfonyl]-1 -[1 -(trifluoroacetyl)-4-piperidinyl]-2,3- dihydro-1H-indoleTo a solution of 1-[1-(trifluoroacetyl)-4-piperidinyl]-2,3-dihydro-1 H-indole-6-sulfonyl chloride (which may be prepared as described for Intermediate 4, 150mg, 0.38mmol) in DCM (1 OmL) was added triethylamine (132mul_, 0.95mmol) followed by 3,3- difluoropiperidine hydrochloride (71 mg, 0.45mmol). The mixture was stirred at room temperature under argon for 2 hours. It was then shaken with 1 M aqueous HCI (1OmL); the DCM layer was isolated and concentrated in vacuo. The resultant yellow oil was purified by flash chromatography on silica gel (25+S, SP4) eluting with a solvent gradient of 0 to 50% ethyl acetate/hexane to afford the title compound as a yellow oil (157mg, 86%).1H NMR (CDCI3, 400MHz): delta 1.59-1.73 (2H, m, partially obscured by H2O), 1.77-1.98 (6H, m), 2.88 (1 H, t, J=13.0), 3.01-3.12 (4H, m), 3.22-3.34 (3H, m), 3.41-3.51 (2H, m), 3.73 (1 H, tt, J=12.0, 4.0), 4.11-4.19 (1 H, m, partially obscured by EtOAc), 4.71 (1 H, m), 6.70 (1 H, d, J=1.5), 6.02 (1 H, dd, J=7.5, 1.5), 7.15 (1 H, m). Mass spectrum (ESI): C20H24F5N3O3S requires 481 ; found 482 (MH+).
86% With triethylamine; In dichloromethane; at 20℃; for 2h; Intermediate 6; 6-[(3,3-Difluoro-1 -piperidinyl)sulfonyl]-1 -[1 -(trifluoroacetyl)-4-piperidinyl]-2,3- dihydro-1H-indoleTo a solution of 1-[1-(trifluoroacetyl)-4-piperidinyl]-2,3-dihydro-1 H-indole-6-sulfonyl chloride (which may be prepared as described for Intermediate 4, 150mg, 0.38mmol) in DCM (1 OmL) was added triethylamine (132mul_, 0.95mmol) followed by 3,3- difluoropiperidine hydrochloride (71 mg, 0.45mmol). The mixture was stirred at room temperature under argon for 2 hours. It was then shaken with 1 M aqueous HCI (1OmL); the DCM layer was isolated and concentrated in vacuo. The resultant yellow oil was purified by flash chromatography on silica gel (25+S, SP4) eluting with a solvent gradient of 0 to 50% ethyl acetate/hexane to afford the title compound as a yellow oil (157mg, 86%).1H NMR (CDCI3, 400MHz): delta 1.59-1.73 (2H, m, partially obscured by H2O), 1.77-1.98 (6H, m), 2.88 (1 H, t, J=13.0), 3.01-3.12 (4H, m), 3.22-3.34 (3H, m), 3.41-3.51 (2H, m), 3.73 (1 H, tt, J=12.0, 4.0), 4.11-4.19 (1 H, m, partially obscured by EtOAc), 4.71 (1 H, m), 6.70 (1 H, d, J=1.5), 6.02 (1 H, dd, J=7.5, 1.5), 7.15 (1 H, m). Mass spectrum (ESI): C20H24F5N3O3S requires 481 ; found 482 (MH+).
  • 10
  • [ 496807-97-7 ]
  • C27H30F4N2O5 [ No CAS ]
  • C32H39F6N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; In dichloromethane; at 20℃; for 18h; To a mixture of aldehyde 33a1 (40 mg, 0.07 mmol) and <strong>[496807-97-7]3,3-difluoropiperidine hydrochloride</strong> (47 mg, 0.30 mmol) in DCM (1 mL) is added NaHB(OAc)3 (31 mg, 0.15 mmol). The mixture is stirred at RT for about 18 hours. Tetrahydrofuran (2 mL), MeOH (1 mL), NaOH (1 N, 1 mL, 1.0 mmol) and LiOH-H2O (15 mg, 0.35 mmol) are added and the mixture is stirred for 3 hours. The mixture is concentrated, taken-up in AcOH (2.5 mL), filtered then injected onto a preparative HPLC to isolate compound 1117.
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; ;