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[ CAS No. 287714-35-6 ] {[proInfo.proName]}

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Chemical Structure| 287714-35-6
Chemical Structure| 287714-35-6
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Product Details of [ 287714-35-6 ]

CAS No. :287714-35-6 MDL No. :MFCD08690330
Formula : C6H5ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :VJOKXLBQCKCWLV-UHFFFAOYSA-N
M.W :172.57 Pubchem ID :12627752
Synonyms :

Calculated chemistry of [ 287714-35-6 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.32
TPSA : 52.08 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) : -6.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 0.99
Log Po/w (WLOGP) : 0.92
Log Po/w (MLOGP) : 0.15
Log Po/w (SILICOS-IT) : 1.38
Consensus Log Po/w : 1.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.81
Solubility : 2.7 mg/ml ; 0.0157 mol/l
Class : Very soluble
Log S (Ali) : -1.67
Solubility : 3.67 mg/ml ; 0.0213 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.34
Solubility : 0.789 mg/ml ; 0.00457 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.47

Safety of [ 287714-35-6 ]

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 [ 287714-35-6 ]

* 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 [ 287714-35-6 ]
  • Downstream synthetic route of [ 287714-35-6 ]

[ 287714-35-6 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 287714-35-6 ]
  • [ 5188-07-8 ]
  • [ 38275-41-1 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 1999, vol. 35, # 11, p. 1334 - 1336
  • 2
  • [ 308348-93-8 ]
  • [ 287714-35-6 ]
YieldReaction ConditionsOperation in experiment
44.4%
Stage #1: With hydrogenchloride; zinc(II) chloride In dichloromethane at 5 - 20℃; for 0.5 h;
Stage #2: at 5 - 10℃; for 2 h;
Step 3a. 2-Chloro-pyrimidine-5-carboxylic acid methyl ester (compound 1001-7) The above intermediate (7 g, 0.046 mol) was added to a mixture of concentrated hydrochloric acid (15.2 mL) and CH2Cl2(60 mL). After cooling, ZnCl2 (18.6 g, 0.138 mol) was added at 15-20° C. The mixture was stirred at 15-20° C. for 0.5 h and cooled to 5-10° C. NaNO2 (9.5 g, 0.138 mol) was added portion wise while keeping the internal temperature 5-10° C. The reaction was continued for 2 h. The reaction mixture was poured into ice-water (50 mL). The organic layer was separated and the aqueous phase was extracted with CH2Cl2 (30 mL×2). The combined organic extracts were concentrated to afford crude product (4.2 g). The crude compound was suspended in hexane (20 mL), heated at 60° C. for 30 minutes and filtered. The filtrate was concentrated to afford the titled compound 1001-7 (3.5 g, 44.4percent) as an off-white solid. LCMS: m/z 214.1 [M+42]+. 1HNMR (400 MHz, CDCl3): δ 4.00 (s, 3H), 9.15 (s, 2H
44.4%
Stage #1: With hydrogenchloride; zinc(II) chloride In dichloromethane; water at 15 - 20℃; for 0.5 h; Cooling
Stage #2: With sodium nitrite In dichloromethane; water at 5 - 10℃; for 2 h;
Step g:
Methyl 2-chloropyrimidine-5-carboxylate (Compound R-2-2)
Compound 207 (7 g, 0.046 mol) was added to a mixture of concentrated hydrochloric acid (15.2 mL) and CH2Cl2 (60 mL).
After cooling, ZnCl2 (18.6 g, 0.138 mol) was added at 15-20° C.
The mixture was stirred at 15-20° C. for 0.5 h and cooled to 5-10° C. NaNO2 (9.5 g, 0.138 mol) was added portion wise while keeping the internal temperature 5-10° C.
The reaction was continued for ˜2 h.
The reaction mixture was poured into ice-water (50 mL).
The organic layer was separated and the aqueous phase was extracted with CH2Cl2 (30 mL*2).
The combined organic extracts were concentrated to afford crude product (4.2 g).
The crude compound was suspended in hexane (20 mL), heated at 60° C. for 30 minutes and filtered.
The filtrate was concentrated to afford the title compound R-2-2 (3.5 g, 44.4percent) as an off-white solid. LCMS (m/z): 214.1[M+42]+. 1HNMR (400 MHz, CDCl3): δ 4.00 (s, 3H), 9.15 (s, 2H).
44.4%
Stage #1: With hydrogenchloride; zinc(II) chloride In dichloromethane; water at 15 - 20℃; for 0.5 h;
Stage #2: With sodium nitrite In dichloromethane at 5 - 10℃; for 2 h;
Compound 207 (7 g, 0.046 mol) was added to a mixture of concentratedhydrochloric acid (15.2 mL) and CH2C12(60 mL). After cooling, ZnC12 (18.6 g, 0.138mol) was added at 15-20 °C. The mixture was stirred at 15-20 °C for 0.5 h and cooled to 5-10 °C. NaNO2 (9.5 g, 0.138 mol) was added portion wise while keeping the internaltemperature 5-10 °C. The reaction was continued for 2 h. The reaction mixture was poured into ice-water (50 mL). The organic layer was separated and the aqueous phase was extracted with CH2C12 (30 nL*2) The combined organic extracts were concentrated to afford cmde product (4.2 g). The crude compound was suspended in hexane (20 mL), heated at 60 °C for 30 minutes and filtered. The filtrate was concentrated to afford the title compound R-2-2 (3.5 g, 44.4 percent) as an off-white solid. LCMS (m/z): 214.1[M+42f. ‘H1’MR (400 MHz, CDC13): ö 4.00 (s, 3H), 9.15 (s, 2H).
Reference: [1] Patent: US2014/18368, 2014, A1, . Location in patent: Paragraph 0162; 0179
[2] Patent: US9249156, 2016, B2, . Location in patent: Page/Page column 35
[3] Patent: WO2018/85342, 2018, A1, . Location in patent: Page/Page column 26; 28; 29
  • 3
  • [ 67-56-1 ]
  • [ 287714-35-6 ]
Reference: [1] Patent: WO2008/156715, 2008, A1, . Location in patent: Page/Page column 67
  • 4
  • [ 18107-18-1 ]
  • [ 287714-35-6 ]
YieldReaction ConditionsOperation in experiment
720 mg at 20℃; for 0.5 h; 2-Chloropyrimidine-5-carboxylic acid (1.00 g)Trimethylsilyl diazomethane (2 M hexane solution, 9.46 mL) was added to a methanol (15 mL) and benzene (37 mL) solution, and the mixture was stirred at room temperature for 30 minutes. After concentrating the reaction solution under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate / hexane) to give the title compound (720 mg) as a white solid.
Reference: [1] Patent: JP2016/141632, 2016, A, . Location in patent: Paragraph 0500; 0502
  • 5
  • [ 287714-35-6 ]
  • [ 1046816-75-4 ]
Reference: [1] Patent: WO2008/97428, 2008, A2, . Location in patent: Page/Page column 128
[2] Patent: WO2011/147951, 2011, A1, . Location in patent: Page/Page column 57; 58
  • 6
  • [ 287714-35-6 ]
  • [ 1339928-25-4 ]
Reference: [1] Patent: US9249156, 2016, B2,
[2] Patent: WO2018/85342, 2018, A1,
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