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[ CAS No. 1007346-33-9 ]

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Chemical Structure| 1007346-33-9
Chemical Structure| 1007346-33-9
Structure of 1007346-33-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1007346-33-9 ]

CAS No. :1007346-33-9 MDL No. :MFCD00105294
Formula : C4H3BrN2O Boiling Point : -
Linear Structure Formula :- InChI Key :UWGFONONBAIDAF-UHFFFAOYSA-N
M.W :174.98 Pubchem ID :2782154
Synonyms :

Calculated chemistry of [ 1007346-33-9 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 31.68
TPSA : 45.75 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) : -6.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.42
Log Po/w (XLOGP3) : 0.7
Log Po/w (WLOGP) : 0.98
Log Po/w (MLOGP) : -0.17
Log Po/w (SILICOS-IT) : 1.88
Consensus Log Po/w : 0.76

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.76
Solubility : 3.02 mg/ml ; 0.0173 mol/l
Class : Very soluble
Log S (Ali) : -1.24
Solubility : 10.1 mg/ml ; 0.0578 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.03
Solubility : 1.63 mg/ml ; 0.00929 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.28

Safety of [ 1007346-33-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1007346-33-9 ]

* 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.

  • Downstream synthetic route of [ 1007346-33-9 ]

[ 1007346-33-9 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 1007346-33-9 ]
  • [ 877680-36-9 ]
  • 4-(2,4-Dimethylphenyl)-1-(4-bromo-1H-pyrazol-5-ylmethylidene)thiosemicarbazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% 57 4-(2,4-Dimethylphenyl)-1-(4-bromo-1H-pyrazol-5-ylmethylidene)thiosemicarbazide EXAMPLE 57 4-(2,4-Dimethylphenyl)-1-(4-bromo-1H-pyrazol-5-ylmethylidene)thiosemicarbazide The title compound was prepared from a mixture of 2,4-dimethylphenylthiosemicarbazide (50 mg, 0.256 mmol) and 4-bromo-1H-pyrazole-5-carboxaldehyde (54 mg, 0.31 mmol) similar to Example 3 and isolated as an off-white solid (67 mg, 74%). 1H NMR (DMSO-d6): 9.98 (s, 1H), 8.15 (s, 1H), 8.02 (s, 1H), 7.86 (s, 1H), 7.16-7.03 (m, 3H), 3.85 (m, 4H), 3.13 (m, 4H), 2.30 (s, 3H), 2.18 (s, 3H).
  • 2
  • [ 1007346-33-9 ]
  • [ 76513-69-4 ]
  • [ 1007346-34-0 ]
YieldReaction ConditionsOperation in experiment
69% Stage #1: 4-bromo-1H-pyrazole-5-carboxaldehyde With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran for 2h; 116.1 Preparation of 4-bromo-l-{ [2- (trimethylsilyl) ethoxy]methyl}- lH-pyrazole-5-carbaldehyde To a stirred suspension of 4-bromo-lH-pyrazole-5- carbaldehyde (1.93 g, 11 iranol) in THF (50 mL) was added sodium hydride (0.484 g, 12.1 mmol) at 00C. After 10 min, [2-(chloromethoxy)ethyl] (trimethyl) silane (2.34 mL, 13.2 mmol) was added. After 2 h, the mixture was poured into saturated aqueous NaHCO3 and extracted with EtOAc (100 mL) , and the extract was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, hexane to 80:20 hexane/EtOAc) to afford the title compound (2.30 g, 69%) as a colorless oil:1H NMR (300 MHz, CDCl3) δ 0.00 (9H, s) , 0.94 (2H, t, J = 8.1 Hz), 3.60 (2H, t, J = 8.1 Hz), 5.48 (2H, s) , 7.70 (IH, s) , 10.00 (IH, s).
39% With sodium hydride In N,N-dimethyl-formamide at 20℃; for 18h;
  • 3
  • [ 1007346-33-9 ]
  • [ 959756-34-4 ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate; acetic acid In isopropyl alcohol 25 EXAMPLE 25 The tert-butyl 4-[4-bromo-3-(hydroxymethyl)pyrazol-1-yl]piperidine-1-carboxylate used as starting materials were made as follows: Sodium tetrahydroborate (35.7 mg) was added to 4-bromo-2H-pyrazole-3-carbaldehyde (150 mg) suspended in 2-propanol (10 ml). The resulting suspension was stirred at 25° C. for 1 hour. A few drops of acetic acid were added and the solution was concentrated to dryness. The crude product was purified by flash chromatography on silica gel eluding with 100% ethyl acetate. The solvent was evaporated to dryness to afford (4-bromo-2H-pyrazol-3-yl)methanol (110 mg). NMR Spectrum: (DMSO-d6+TFAd) 4.44 (s, 2H), 7.69 (s, 1H); Mass spectrum: M+H+ 177-179.
With sodium tetrahydroborate In tetrahydrofuran at 50℃; for 1h; 12.1 (4-Bromo-1H-pyrazol-5-yl)methanol Sodium tetrahydroborate (0.13 g, 3.4 mmol) was added to a solution of 4-bromo-1H-pyrazole-5-carbaldehyde (0.30 g, 1.7 mmol, from Maybridge) in tetrahydrofuran (5 mL). The reaction mixture was stirred at 50° C. for 1 h. The reaction mixture was quenched with saturated aqueous NaHCO3, and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford the crude product which was directly used in the next step reaction without further purification. LCMS calculated for C4H6BrN2O (M+1)+: m/z=177.0. Found: 176.9.
  • 4
  • [ 1007346-33-9 ]
  • [ 141699-59-4 ]
  • [ 1146951-48-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetonitrile 60 1-[4-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]-1-(4-piperidyl)pyrazol-3-yl]ethanol The tert-butyl 4-[4-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]-3-(1-hydroxyethyl)pyrazol-1-yl]piperidine-1-carboxylate used as starting material was prepared as follows: 4-bromo-2H-pyrazole-3-carbaldehyde (3 g), potassium carbonate (3.32 g) and tert-butyl 4-methylsulfonyloxypiperidine-1-carboxylate (6.23 g) in acetonitrile (150 ml) were stirred at reflux overnight. The resulting precipitate was removed by filtration and the filtrate was concentrated and purified by flash chromatography on silica gel eluding with 0 to 20% ethyl acetate in petroleum ether.
  • 5
  • [ 1007346-33-9 ]
  • (R)-2-(benzylamino)propan-1-ol-2-d [ No CAS ]
  • (R)-2-(benzyl((4-bromo-1H-pyrazol-5-yl)methyl)amino)propan-1-ol-2-D [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 25℃; for 2.5h;
  • 6
  • [ 287917-97-9 ]
  • [ 74609-49-7 ]
  • (R)-2-(benzyl((4-bromo-1H-pyrazol-5-yl)methyl)amino)propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With sodium tris(acetoxy)borohydride; at 20℃; for 3h; (R)-2-(Benzylamino)propan-1-ol (800 mg, 4.8 mmol)And 3-aldehyde-4-bromopyrazole (703 mg, 4 mmol) were added to a solution of 1,1-dichloroethane (15 mL), respectively.Sodium triacetoxyborohydride (2.55 g, 12 mmol) was then added to the reaction mixture and allowed to react at room temperature for 3 h.The reaction mixture was diluted with water and extracted with dichloromethane (3×).The organic phase is filtered, concentrated under reduced pressure and purified by silica gel column to give product(R)-2-(Benzyl((4-bromo-1H-pyrazol-5-yl)methyl)amino)propan-1-ol (905 mg, yield 73%).
70% With sodium tris(acetoxy)borohydride; In methanol; at 20℃; for 2h; 4-bromopyrazole-5-carboxaldehyde (875 mg, 5 mmol) and <strong>[74609-49-7](R)-2-(benzylamino)propan-1-ol</strong> (996 mg, 6 mmol) were added to a solution of methanol (20 mL). Sodium triacetoxyborohydride (3.18 g, 15 mmol) was then added to the reaction mixture. After reacting for 3 h at room temperature, the reaction mixture was diluted with water and extracted three times with ethyl acetate. The organic phase was combined and dried over anhydrous Na2SO4. (R)-2-(Benzyl((4-bromo-1H-pyrazol-5-yl)methyl)amino)propan-1-ol (1.13 g, yield 70%).
  • 7
  • [ 287917-97-9 ]
  • [ 115643-59-9 ]
  • C11H6BrFN4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium metabisulfite; In N,N-dimethyl acetamide; for 5h;Inert atmosphere; Reflux; Under the argon 2-amino-6-fluoro-benzamide (77 mg, 0 . 50mmol) dissolved in dimethylacetamide (5 ml) in, by adding 4-bromo -1H-pyrazole-5-formaldehyde (88 mg, 0 . 50mmol) and Na 2 S 2 O 5 (143 mg, 0 . 75mmol), and the mixture stirred under the reflow conditions for 5 hours. After the cooling to room temperature, the reaction mixture is concentrated, and dissolved in acetonitrile and N, N-dimethyl formamide in a mixture. Filtered and thoroughly drying the remaining solid, get colorless solid 2 - (4-bromo -1H-pyrazol-5-yl) - 5- [...] -4 (3H)-one (30 mg, of the setpoint value of 19%). 1 HNMR (400MHz, d 6-DMSOdelta, PPM) 13.91 (br.s, 1H, NH), 12.03 (br.s, 1H, NH), 8.22 (s, 1H), 7.80 (dd, 1H), 7.51 (d, 1H), 7.27 (dd, 1H).
  • 8
  • [ 1007346-33-9 ]
  • C51H79N12O21PS [ No CAS ]
  • C55H80BrN14O21PS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In dimethyl sulfoxide at 20℃; for 24h;
  • 9
  • [ 1007346-33-9 ]
  • C52H83N12O19PS [ No CAS ]
  • C56H84BrN14O19PS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In dimethyl sulfoxide at 20℃; for 24h;
  • 10
  • [ 1007346-33-9 ]
  • C53H83N12O21PS [ No CAS ]
  • C57H84BrN14O21PS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In dimethyl sulfoxide at 20℃; for 24h;
  • 11
  • [ 1007346-33-9 ]
  • C52H83N12O19PS [ No CAS ]
  • C56H84BrN14O19PS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In dimethyl sulfoxide at 20℃; for 24h;
  • 12
  • [ 1007346-33-9 ]
  • C51H81N12O19PS [ No CAS ]
  • C55H82BrN14O19PS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In dimethyl sulfoxide at 20℃; for 24h;
  • 13
  • [ 1007346-33-9 ]
  • C50H77N12O21PS [ No CAS ]
  • C54H78BrN14O21PS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In dimethyl sulfoxide at 20℃; for 24h;
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