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CAS No. : | 70500-80-0 | MDL No. : | MFCD07388488 |
Formula : | C7H11N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KTRQSZBRYRHIKL-UHFFFAOYSA-N |
M.W : | 169.18 | Pubchem ID : | 14877880 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.43 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 43.98 |
TPSA : | 70.14 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.02 cm/s |
Log Po/w (iLOGP) : | 1.59 |
Log Po/w (XLOGP3) : | 0.44 |
Log Po/w (WLOGP) : | 0.19 |
Log Po/w (MLOGP) : | 0.18 |
Log Po/w (SILICOS-IT) : | -0.21 |
Consensus Log Po/w : | 0.44 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.28 |
Solubility : | 8.95 mg/ml ; 0.0529 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.48 |
Solubility : | 5.59 mg/ml ; 0.0331 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.91 |
Solubility : | 20.7 mg/ml ; 0.122 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.13 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62.9% | To the resulting residue are added an aqueous sodium bicarbonate solution and an aqueous sodium chloride solution, and the mixture is extracted 6 times with chloroform, dried with magnesium sulfate, and chromatographed on a column of silica gel. The ethyl acetate elude gives 6.54 g (62.9% yield) of the objective compound 11 as an yellow oil. NMR: deltaCDCl 3 1.35 (3H, t), 3.71 (3H, s), 3.76 (2H, bs), 4.35 (2H, q), 6.03 (1H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl acetamide; at 125℃; for 2h;Inert atmosphere; Sealed tube; | A mixture of 6-chloro-N-cyclopropyl-8-((4-methoxybenzyl)(methyl) amino)imidazo [1 ,2-bjpyridazine-3 -carboxamide (id) (125 mg, 0.324 mmol), ethyl 5-amino-i-methyl- 1H-pyrazole-3 -carboxylate [Free based (sodium bicarbonate solutionlEtOAc) from HC1 salt purchased from Acorn Pharma. Tech.j (88 mg, 0.5 18 mmol), Pd2(dba)3 (29.7 mg, 0.032 mmol), XANTPHOS (37.5 mg, 0.065 mmol) and Cs2CO3 (422 mg, 1.296 mmol) in DMA (2 mL) was degassed by bubbling N2 through the mixture for 5 minutes. The reaction vessel was sealed and heated to 125 C for 2 hr. After cooling to rt, the reaxtion mixture was partitioned between EtOAc (50 ml) and water (50 ml). The organic layer was washed with 10%LiC1 solution (2 x 50 ml) and brine (50 ml). After drying (Na2SO4) and filtration the organic layer was concentrated toafford a tan solid that was chromatographed on a 12 gm ISCO silica gel cartridge, eluting with a 0-1 OO%EtOAc/Hex gradient. The pure fractions were concentrated to afford ethyl 5 -((3-(cyclopropylcarbamoyl)-8-((4-methoxybenzyl)(methyl)amino)imidazo [1,2- bjpyridazin-6-yl)amino)- 1-methyl-i H-pyrazole-3 -carboxylate (39a) (126 mg, 0.243 mmol, 75 % yield) as atan solid. LC retention time 2.77 mm [Cj. MS (E+) m/z: 519(MHj. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | To a mixture of methylhydrazine (13.47 g, 116.92 mmol, 15.4 mL, 1.1 eq) in methanol (150 mL) was added sulfuric acid (10.42 g, 106.29 mmol, 5.6 mL, 1 eq) dropwise at 0 C. The mixture was stirred at 25 C for 0.5 h, then ethyl 3-cyano-2-oxo-propanoate (15 g, 106.29 mmol, 1 eq) was added at 25 C and the mixture was stirred at 25 C for 20.5 hours. The mixture was concentrated in vacuum. The residue was purified by silica gel column (3764) chromatography (petroleum ether: ethyl acetate=20:1~1:2). The product ethyl 5-amino-1-methyl- pyrazole-3-carboxylate (11.9 g, 70.34 mmol, 66% yield) was obtained as brown oil. LC/MS (ESI) m/z: 170.2 [M+1] +; 1H-NMR (400MHz, CDCl3) d 6.16 - 6.05 (m, 1H), 4.47 - 4.32 (m, 2H), 3.83 - 3.68 (m, 3H), 3.28 - 3.14 (m, 2H), 1.44 - 1.35 (m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With methanol; 2-picoline borane complex; acetic acid; at 25℃; for 12h; | To a solution of benzyl N,N-bis(2-oxoethyl)carbamate (14.8 g, 62.92 mmol, 1.1 eq) and ethyl 5-amino-1-methyl-pyrazole-3-carboxylate (9.68 g, 57.20 mmol, 1 eq) in acetic acid (20 mL) and methanol (280 mL) was added borane;2-methylpyridine (12.24 g, 114.39 mmol, 2 eq). The mixture was stirred at 25 C for 1 h. And then the mixture was stirred at 25 C for 11 h. Saturated aqueous sodium bicarbonate (~180 mL) was added into the mixture to adjust the pH=8. The aqueous phase was extracted with ethyl acetate (300 mL x 3). The combined organic phase was washed with brine (500 mL x 2), dried with anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography (petroleum ether/ ethyl acetate=30/1, 1/1). The oil was further purified by preparative reverse phase HPLC. The solution was concentrated in vacuum. The aqueous phase was extracted with ethyl acetate (200 mL x 3). The combined organic phase was washed with brine (200 mL x 2), dried with anhydrous sodium sulfate, filtered and concentrated in vacuum. The product benzyl 4-(5- ethoxycarbonyl-2-methyl-pyrazol-3-yl)piperazine-1-carboxylate (11.55 g, 31.01 mmol, 54% yield) was obtained as a colorless oil. LC/MS (ESI) m/z: 373.3 [M+1] +. |
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