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[ CAS No. 394223-15-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 394223-15-5
Chemical Structure| 394223-15-5
Chemical Structure| 394223-15-5
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Product Details of [ 394223-15-5 ]

CAS No. :394223-15-5 MDL No. :MFCD08690236
Formula : C7H4N2OS Boiling Point : -
Linear Structure Formula :- InChI Key :BWKIBIZZLRPKFY-UHFFFAOYSA-N
M.W : 164.18 Pubchem ID :18504697
Synonyms :

Calculated chemistry of [ 394223-15-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.8
TPSA : 71.09 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.36 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.44
Log Po/w (XLOGP3) : 1.33
Log Po/w (WLOGP) : 1.5
Log Po/w (MLOGP) : 0.43
Log Po/w (SILICOS-IT) : 2.8
Consensus Log Po/w : 1.5

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.24
Solubility : 0.955 mg/ml ; 0.00582 mol/l
Class : Soluble
Log S (Ali) : -2.42
Solubility : 0.618 mg/ml ; 0.00377 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.54
Solubility : 0.477 mg/ml ; 0.0029 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.96

Safety of [ 394223-15-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P272-P280-P302+P352-P333+P313-P363-P501 UN#:
Hazard Statements:H317 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 394223-15-5 ]

* 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 [ 394223-15-5 ]

[ 394223-15-5 ] Synthesis Path-Downstream   1~8

  • 2
  • [ 23616-15-1 ]
  • [ 394223-15-5 ]
YieldReaction ConditionsOperation in experiment
20.a (a) (a) Benzo[1,2,3]thiadiazole-5-carboxaldehyde This was prepared from methyl benzo[1,2,3]thiadiazole-5-carboxylate (0.291 g) by the method of Example 16c, (except that the alcohol was stirred with manganese (II) oxide overnight) and used without purification.
  • 3
  • [ 394223-15-5 ]
  • [ 615568-10-0 ]
  • [ 944407-64-1 ]
  • 1-({4-[(1,2,3-benzothiadiazol-5-ylmethyl)amino]-1-piperidinyl}methyl)-9-fluoro-1-hydroxy-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one Dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride In methanol; dichloromethane 23 Example 23 Example 23 1-({4-[(1,2,3-benzothiadiazol-5-ylmethyl)amino]-1-piperidinyl}methyl)-9-fluoro-1-hydroxy-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one Dihydrochloride A solution of 1-[(4-amino-1-piperidinyl)methyl]-9-fluoro-1-hydroxy-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (racemic) (48 mg, 0.15 mmol) and 1,2,3-benzothiadiazole-5-carbaldehyde (prepared by manganese (IV) oxide oxidation of benzo[1,2,3]thiadiazol-5-yl-methanol, for a synthesis see Example 6(a)) (25 mg, 0.15 mmol) in dichloromethane (3 ml) and methanol (1 ml) was treated with sodium triacetoxyborohydride (95 mg, 0.45 mmol) for 5 hours at room temperature. Excess sodium bicarbonate solution was added and the mixture evaporated to dryness. The residue was chromatographed on silica gel, eluding with 0-50% methanol in dichloromethane, affording the free base as an oil (25 mg, 36%). MS (+ve ion electrospray) m/z 466 (MH+). δ H (CDCl3, 250MHz) 1.51 (2H, m), 1.95-2.25 (m, signals partly obscured by a water peak), 2.38 (1H, t), 2.55 (1H, t), 2.65 (2H, m), 2.85 (1H, d), 3.0 (2H, br.d), 3.36 (1H, d), 4.05 (2H, s), 4.40 (2H, m), 6.62 (1H, d), 6.90 (1H, t), 7.50 (1H, q), 7.70 (2H, m), 8.05 (1H, d), 8.60 (1H, s). The free base in methanol, was converted to the dihydrochloride salt by adding an excess of 1M hydrogen chloride in ether, followed by evaporation to dryness, to give a solid (30 mg).
  • 4
  • [ 394223-15-5 ]
  • [ 944407-64-1 ]
  • [ 944406-75-1 ]
YieldReaction ConditionsOperation in experiment
36% With sodium tris(acetoxy)borohydride In methanol; dichloromethane at 20℃; for 5h; 23 Example 23 1-({4-[(1,2,3-benzothiadiazol-5-ylmethyl)amino]-1-piperidinyl}methyl)-9-fluoro-1-hydroxy-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one Dihydrochloride A solution of 1-[(4-amino-1-piperidinyl)methyl]-9-fluoro-1-hydroxy-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (racemic) (48 mg, 0.15 mmol) and 1,2,3-benzothiadiazole-5-carbaldehyde (prepared by manganese (IV) oxide oxidation of benzo[1,2,3]thiadiazol-5-yl-methanol, for a synthesis see WO2003087098 Example 6(a)) (25 mg, 0.15 mmol) in dichloromethane (3 ml) and methanol (1 ml) was treated with sodium triacetoxyborohydride (95 mg, 0.45 mmol) for 5 hours at room temperature. Excess sodium bicarbonate solution was added and the mixture evaporated to dryness. The residue was chromatographed on silica gel, eluting with 0-50% methanol in dichloromethane, affording the free base as an oil (25 mg, 36%).MS (+ve ion electrospray) m/z 466 (MH+).δH (CDCl3, 250 MHz) 1.51 (2H, m), 1.95-2.25 (m, signals partly obscured by a water peak), 2.38 (1H, t), 2.55 (1H, t), 2.65 (2H, m), 2.85 (1H, d), 3.0 (2H, br.d), 3.36 (1H, d), 4.05 (2H, s), 4.40 (2H, m), 6.62 (1H, d), 6.90 (1H, t), 7.50 (1H, q), 7.70 (2H, m), 8.05 (1H, d), 8.60 (1H, s).The free base in methanol, was converted to the dihydrochloride salt by adding an excess of 1M hydrogen chloride in ether, followed by evaporation to dryness, to give a solid (30 mg).
  • 5
  • [ 615568-10-0 ]
  • [ 394223-15-5 ]
YieldReaction ConditionsOperation in experiment
With manganese(IV) oxide 23 Example 23 1-({4-[(1,2,3-benzothiadiazol-5-ylmethyl)amino]-1-piperidinyl}methyl)-9-fluoro-1-hydroxy-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one Dihydrochloride A solution of 1-[(4-amino-1-piperidinyl)methyl]-9-fluoro-1-hydroxy-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (racemic) (48 mg, 0.15 mmol) and 1,2,3-benzothiadiazole-5-carbaldehyde (prepared by manganese (IV) oxide oxidation of benzo[1,2,3]thiadiazol-5-yl-methanol, for a synthesis see WO2003087098 Example 6(a)) (25 mg, 0.15 mmol) in dichloromethane (3 ml) and methanol (1 ml) was treated with sodium triacetoxyborohydride (95 mg, 0.45 mmol) for 5 hours at room temperature. Excess sodium bicarbonate solution was added and the mixture evaporated to dryness. The residue was chromatographed on silica gel, eluting with 0-50% methanol in dichloromethane, affording the free base as an oil (25 mg, 36%).MS (+ve ion electrospray) m/z 466 (MH+).δH (CDCl3, 250 MHz) 1.51 (2H, m), 1.95-2.25 (m, signals partly obscured by a water peak), 2.38 (1H, t), 2.55 (1H, t), 2.65 (2H, m), 2.85 (1H, d), 3.0 (2H, br.d), 3.36 (1H, d), 4.05 (2H, s), 4.40 (2H, m), 6.62 (1H, d), 6.90 (1H, t), 7.50 (1H, q), 7.70 (2H, m), 8.05 (1H, d), 8.60 (1H, s).The free base in methanol, was converted to the dihydrochloride salt by adding an excess of 1M hydrogen chloride in ether, followed by evaporation to dryness, to give a solid (30 mg).
  • 6
  • [ 394223-15-5 ]
  • (1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione dihydrochloride [ No CAS ]
  • [ 1075236-83-7 ]
YieldReaction ConditionsOperation in experiment
36% Stage #1: (1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione dihydrochloride With triethylamine In methanol; chloroform at 20℃; for 15h; Stage #2: benzo[d] [1,2,3 ]thiadiazole-5-carbaldehyde In methanol; chloroform for 0.5h; Stage #3: With water; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate more than 3 stages; 35 Example 35; (lR)-l-({4-[(l,2,3-Benzothiadiazol-5-ylmethyl)amino]-l- piperidinyl} methyl)- 1 ,2-dihydro-4H,9H-imidazo [1 ,2,3-//] - 1 ,8-naphthyridine-4,9- dione hydrochloride; A suspension of (li?)-l-( {4-[(l,2,3-benzothiadiazol-5-ylmethyl)amino]-l- piperidinyl}methyl)-l ,2-dihydro-4η,9η-imidazo[ 1 ,2,3-ij]- 1 ,8-naphthyridine-4,9-dione dihydrochoride (for a preparation see Example 5A(j)) (60mg, 0.161 mmol) in chloroform (2 ml) and methanol (0.100 ml) at rt under nitrogen was treated with triethylamine (0.067 ml, 0.482 mmol) and stirred at rt for 15h. The solution was then treated with 1,2,3- benzothiadiazole-5-carbaldehyde (for a synthesis see WO0208224 Example 20(a)) (23.75 mg, 0.145 mmol) and stirred for a further 30min. The solution was then treated with sodium triacetoxyborohydride (102 mg, 0.482 mmol) and stirred at rt for 45min, LC-MS after 45min showed reaction complete. This was then treated with saturated aqueous NaHCO3 (10ml) and extracted with 20% methanol/DCM (3 x 25ml). The combined organic extracts were dried (MgSO4), filtered, evaporated and chromato graphed (0-5% methanol/DCM 5%methanol/DCM) to give the free base of the title compound (26mg, 36%) as a pale yellow solid.1H NMR δH CDCl3, (400MHz) 1.30-1.49 (m, 2H),1.80-1.98 (m, 2H), 2.21-2.39 (m, 2H), 2.51-2.61 (m, IH), 2.61-2.75 (m, 2H), 2.90-3.02 (m, IH), 3.05-3.19 (m, IH), 4.04 (s, 2H), 4.31-4.42(m, IH), 4.51-4.61 (m, IH), 4.92-5.05 (m, IH), 6.20-6.31 (m, 2H), 7.45-7.53 (2H, m), 7.71 (d, IH). 8.11 (d, IH), 8.56 (s, IH) MS (ES+) m/z 449 (MH+).The free base of the title compound was dissolved in a small amount of DCM, treated with one equivalent of IM HCl in diethyl ether and then evaporated to give the title compound as the mono-HCl salt (16.2mg, 20.8%). LCMS consistent with product.
26 mg Stage #1: (1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione dihydrochloride With triethylamine In methanol; chloroform at 20℃; for 15h; Inert atmosphere; Stage #2: benzo[d] [1,2,3 ]thiadiazole-5-carbaldehyde In methanol; chloroform for 0.5h; Inert atmosphere; Stage #3: With methanol; sodium tris(acetoxy)borohydride In chloroform at 20℃; for 0.75h; Inert atmosphere; 35 Example 35
(1R)-1-({4-[(1,2,3-Benzothiadiazol-5-ylmethyl)amino]-1-piperidinyl}methyl)-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione hydrochloride A suspension of (1R)-1-({4-[(1,2,3-benzothiadiazol-5-ylmethyl)amino]-1-piperidinyl}methyl)-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione dihydrochoride (for a preparation see Example 5A(j)) (60 mg, 0.161 mmol) in chloroform (2 ml) and methanol (0.100 ml) at rt under nitrogen was treated with triethylamine (0.067 ml, 0.482 mmol) and stirred at rt for 15 h. The solution was then treated with 1,2,3-benzothiadiazole-5-carbaldehyde (for a synthesis see WO0208224 Example 20(a)) (23.75 mg, 0.145 mmol) and stirred for a further 30 min. The solution was then treated with sodium triacetoxyborohydride (102 mg, 0.482 mmol) and stirred at rt for 45 min, LC-MS after 45 min showed reaction complete. This was then treated with saturated aqueous NaHCO3 (10 ml) and extracted with 20% methanol/DCM (3*25 ml). The combined organic extracts were dried (MgSO4), filtered, evaporated and chromatographed (0-5% methanol/DCM 5% methanol/DCM) to give the free base of the title compound (26 mg, 36%) as a pale yellow solid. 1H NMR δH CDCl3, (400 MHz) 1.30-1.49 (m, 2H), 1.80-1.98 (m, 2H), 2.21-2.39 (m, 2H), 2.51-2.61 (m, 1H), 2.61-2.75 (m, 2H), 2.90-3.02 (m, 1H), 3.05-3.19 (m, 1H), 4.04 (s, 2H), 4.31-4.42 (m, 1H), 4.51-4.61 (m, 1H), 4.92-5.05 (m, 1H), 6.20-6.31 (m, 2H), 7.45-7.53 (2H, m), 7.71 (d, 1H). 8.11 (d, 1H), 8.56 (s, 1H) MS (ES+) m/z 449 (MH+).
  • 7
  • [ 394223-15-5 ]
  • [ 347910-45-6 ]
  • [ 1572184-05-4 ]
YieldReaction ConditionsOperation in experiment
65% In ethanol at 100℃; for 16h; 40 Example 40. Synthesis of compound 206 Example 40. Synthesis of compound 2062-(mesityloxy)acetohydrazide (0.10 g, 0.39 mmol) and benzo[d] [1,2,3 ]thiadiazole-5-carbaldehyde (0.079 g, 0.48 mmol) were dissolved in EtOH, followed by stirring at 100 °C for16 hours. After the completion of the reaction, the reaction mixture was cooled to roomtemperature, and concentrated under reduced pressure. The resulting solid was purified by column chromatography and by recrystallization to obtain Compound 206 (0.11 g, 65 %). 1H NMR (400 MHz, DMSO-d6): ö 11.81-11.73 (m, 1H), 8.89-8.85 (m, 1H), 8.69 (s, 0.5H),8.47-8.36 (m, 1H), 8.23-8.07 (s, 1.5H), 6.84-8.8 1 (m, 2H), 4.80-4.36 (m, 2H), 2.22-2.16(m, 9H).
  • 8
  • [ 394223-15-5 ]
  • (1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione dihydrochloride [ No CAS ]
  • [ 1075235-38-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / methanol; chloroform / 15 h / 20 °C 1.2: 0.5 h 2.1: hydrogenchloride / diethyl ether; dichloromethane
Multi-step reaction with 2 steps 1.1: triethylamine / methanol; chloroform / 15 h / 20 °C / Inert atmosphere 1.2: 0.5 h / Inert atmosphere 1.3: 0.75 h / 20 °C / Inert atmosphere 2.1: hydrogenchloride / dichloromethane; diethyl ether
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