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[ CAS No. 1224944-77-7 ] {[proInfo.proName]}

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Chemical Structure| 1224944-77-7
Chemical Structure| 1224944-77-7
Structure of 1224944-77-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1224944-77-7 ]

CAS No. :1224944-77-7 MDL No. :MFCD12407819
Formula : C9H8ClN3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :UOZKVCQDLXBWBG-UHFFFAOYSA-N
M.W : 225.63 Pubchem ID :58063474
Synonyms :

Calculated chemistry of [ 1224944-77-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 54.08
TPSA : 56.49 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) : -6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.2
Log Po/w (XLOGP3) : 1.51
Log Po/w (WLOGP) : 1.56
Log Po/w (MLOGP) : 1.45
Log Po/w (SILICOS-IT) : 1.22
Consensus Log Po/w : 1.59

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.44
Solubility : 0.826 mg/ml ; 0.00366 mol/l
Class : Soluble
Log S (Ali) : -2.3
Solubility : 1.12 mg/ml ; 0.00496 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.82
Solubility : 0.343 mg/ml ; 0.00152 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.08

Safety of [ 1224944-77-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1224944-77-7 ]

* 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.

  • Upstream synthesis route of [ 1224944-77-7 ]
  • Downstream synthetic route of [ 1224944-77-7 ]

[ 1224944-77-7 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 926663-00-5 ]
  • [ 1224944-77-7 ]
YieldReaction ConditionsOperation in experiment
97.6% for 2 h; Reflux Step B: Preparation of ethyl 5 -chloropyrazolo [1,5 -alpyrimidine-3 -carboxylate.; Ethyl 5-hydroxypyrazolo[l,5-a]pyrimidine-3-carboxylate (22.7 g, 110 mmol) was suspended in phosphoryl trichloride (100 mL) and heated to reflux. After heating for 2 hours, the reaction mixture was cooled and concentrated to remove the excess POCI3. The residue was diluted in DCM (100 mL) and slowly added to a flask containing ice water. The mixture was separated and the aqueous layer extracted with DCM. The combined organics were dried with MgSO4, filtered and concentrated to afford ethyl 5-chloropyrazolo[l,5-a]pyrimidine-3- carboxylate (24.2 g, 97.6 percent yield) as a pale yellow solid. MS (apci) m/z = 225.9 (M+H).
61% at 100℃; for 16 h; POCl3 (30 mL, 322 mmol) was added to 30 (5.54 g,26.7 mmol) and the mixture was stirred at 100°C for 16 h.After POCl3 was removed under reduced pressure, the residuewas partitioned between EtOAc and NaHCO3 aqueous solution. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic phases werewashed with water and saturated aqueous NaCl, dried overanhydrous Na2SO4 and concentrated in vacuo. The residuewas purified by column chromatography (silica gel, hexane–ethyl acetate, 19 : 1 to 1 : 1) to afford 36 (3.69 g, 16.3 mmol,61percent) as a white solid. MS (ESI/APCI) m/z 226.1 [M+H]+.
14.05 g With trichlorophosphate In acetonitrile at 10 - 110℃; for 4 h; Inert atmosphere B)
ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate
Ethyl 5-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylate (18.0 g) was suspended in acetonitrile (40 mL), phosphorus oxychloride (40 mL) was added at room temperature, and the mixture was stirred under a nitrogen atmosphere at 110° C. for 4 hr.
The reaction mixture was cooled, and concentrated under reduced pressure.
The residue was diluted with ethyl acetate and neutralized with aqueous sodium bicarbonate solution, and insoluble material was filtered off with Celite.
The organic layer of the filtrate was purified by a silica gel pad, and the solvent was evaporated under reduced pressure.
The precipitated solid was washed with ethyl acetate/diisopropyl ether to give the title compound (14.1 g).
The mother liquor was further concentrated under reduced pressure and the resulting solid was washed with ethyl acetate/diisopropyl ether to give the title compound (2.40 g).
1H NMR (300 MHz, CDCl3) δ 1.42 (3H, t, J=7.2 Hz), 4.43 (2H, q, J=7.2 Hz), 6.99 (1H, d, J=7.2 Hz), 8.56 (1H, s), 8.63 (1H, d, J=7.2 Hz).
14.1 g With trichlorophosphate In acetonitrile at 110℃; for 4 h; The 5-hydroxy pyrazole [1,5-a] pyrimidine-3-carboxylic acid ethyl ester (18.0g) suspended in acetonitrile (40 ml), at room temperature add oxygen phosphorus chloride (40 ml), and to the mixture under nitrogen atmosphere to 110 °C stirring 4 hours. Cooling the reaction mixture, and the concentrated under reduced pressure. Aid hemostasis diluted with ethyl acetate and to neutralize the sodium bicarbonate aqueous solution, but insoluble material to celite filtration. The organic filtrate is purified by silicon rubber, and the evaporation of the solvent under reduced pressure. Precipitation of the solid in ethyl acetate/b isopropyl group ether cleaning in order to produce the title compound (14.1g). Mother liquor further for concentrated under reduced pressure, and the generated solid of using ethyl acetate/b isopropyl group ether cleaning in order to produce the title compound (2.40g).

Reference: [1] Patent: WO2011/6074, 2011, A1, . Location in patent: Page/Page column 70-71
[2] Chemical and Pharmaceutical Bulletin, 2017, vol. 65, # 11, p. 1058 - 1077
[3] Patent: WO2012/34095, 2012, A1, . Location in patent: Page/Page column 68
[4] Patent: US2016/159808, 2016, A1, . Location in patent: Paragraph 1357; 1358; 1381; 1382; 1394; 1395
[5] Patent: TW2016/520, 2016, A, . Location in patent: Paragraph 0165
[6] Patent: WO2018/81417, 2018, A2, . Location in patent: Page/Page column 162; 163
  • 2
  • [ 1260243-04-6 ]
  • [ 1224944-77-7 ]
Reference: [1] Patent: US2016/168156, 2016, A1,
[2] Patent: WO2017/4342, 2017, A1,
[3] Patent: WO2017/15367, 2017, A1,
[4] Patent: WO2013/59587, 2013, A1,
[5] Patent: EP2768509, 2017, B1,
[6] Patent: WO2017/7759, 2017, A1,
[7] Chemical and Pharmaceutical Bulletin, 2017, vol. 65, # 11, p. 1058 - 1077
  • 3
  • [ 6994-25-8 ]
  • [ 1224944-77-7 ]
Reference: [1] Patent: WO2011/6074, 2011, A1,
[2] Patent: WO2012/34095, 2012, A1,
[3] Patent: US2016/159808, 2016, A1,
[4] Patent: TW2016/520, 2016, A,
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