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[ CAS No. 115093-90-8 ] {[proInfo.proName]}

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Chemical Structure| 115093-90-8
Chemical Structure| 115093-90-8
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Product Details of [ 115093-90-8 ]

CAS No. :115093-90-8 MDL No. :MFCD09999173
Formula : C6H3Cl2N3 Boiling Point : -
Linear Structure Formula :- InChI Key :VFTPONHUNNOSKG-UHFFFAOYSA-N
M.W :188.01 Pubchem ID :11106092
Synonyms :

Calculated chemistry of [ 115093-90-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.91
TPSA : 41.57 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) : -5.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.56
Log Po/w (XLOGP3) : 2.25
Log Po/w (WLOGP) : 2.26
Log Po/w (MLOGP) : 1.38
Log Po/w (SILICOS-IT) : 2.85
Consensus Log Po/w : 2.06

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.03
Solubility : 0.176 mg/ml ; 0.000936 mol/l
Class : Soluble
Log S (Ali) : -2.76
Solubility : 0.327 mg/ml ; 0.00174 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.77
Solubility : 0.0318 mg/ml ; 0.000169 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.46

Safety of [ 115093-90-8 ]

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

Application In Synthesis of [ 115093-90-8 ]

* 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 [ 115093-90-8 ]
  • Downstream synthetic route of [ 115093-90-8 ]

[ 115093-90-8 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 3680-69-1 ]
  • [ 115093-90-8 ]
YieldReaction ConditionsOperation in experiment
95% With N-chloro-succinimide In N,N-dimethyl-formamide at 20℃; for 72 h; General procedure: To a solution of readily available 3a (20mmol) in N, N-dimethylformamide (DMF) (15mL) was added NCS/NBS (21mmol) and the reaction mixture was stirred at room temperature for 72h. Then ice water (150mL) was poured into the mixture, the precipitate was filtered, washed with water (3×100mL), and dried to give 3b and 3c.
95% With N-chloro-succinimide In N,N-dimethyl-formamide at 20℃; for 12 h; Dissolve 4-chloro-pyrrolo[2,3-d]pyrimidine (20 mmol) in DMF (6 mL), add NBS or NCS (21 mmol) in portions on ice bath, react at room temperature for 12 h, and pour the reaction mixture into 80 mL of ice. In the water, a large number of off-white solids precipitated and were filtered. The filter cake was washed with 15 mL of water and dried to give Intermediate 2. 4,5-dichloro-pyrrolo[2,3-d]pyrimidine (2a) Gray solid, yield 95percent
88% With N-chloro-succinimide In dichloromethane for 72 h; Heating / reflux 3H, m), 2.4 (3H, s), 1.31 (3H, J=6.8 Hz, d); MS (ES+) [M+H]+=455.6.15. Example 15(S)-N-(3-bromophenyl)-4-(5-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N'-cyano-2-methylpiperazine-1-carboximidamide A. Preparation of 4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidine: 4-Chloro-pyrrolo[2,3-d]pyrimidine (0.5 g, 3.26 mmol) was suspended in anhydrous CH2Cl2 (25 ml), and N-chlorosuccinimide (0.87 g, 6.52 mmol) was added. The reaction mixture was refluxed for 3 days, then cooled to room temperature. The white solid was collected by filtration to give 5-dichloro-7H-pyrrolo[2,3-d]pyrimidine (0.54 g, 2.9 mmol, 88percent).1H NMR (CD3OD): δ 8.57 (1H, s), 7.60 (1H, s); MS (ES+) [M+H]+=188.
80% With N-chloro-succinimide In dichloromethane at 20℃; for 6 h; Heating / reflux PREPARATION 7; 4,5-dichloro-7H-pyrrolor2,3-dlpyrimidineN-Chlorosuccinimide (4.78 g, 35.81 mmol) was added portionwise to a stirred suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (5g, 32.56 mmol) in DCM, dry (125ml) at room temperature. The resulting suspension was stirred for 1 hour then heated to reflux for 5 hours, then allowed to cool down and left to stir at room temperature overnight. The reaction mixture was evaporated and suspended in water (50 mL). The suspension was filtered giving crude product as a grey solid. The solid was suspended in hot methnol and filtered. The solid was then suspended in hot ethyl acetate and filtered to give 4,5- dichloro-7H-pyrrolo[2,3-d]pyrimidine (4.87 g, 80 percent) as a grey solid. IH NMR (400.13 MHz, DMSO-d6) δ 7.91 (IH, s), 8.64 (IH, s), 12.87 (IH, s) MS m/e MH+ 188
80% With N-chloro-succinimide In dichloromethane at 20℃; Heating / reflux PREPARATION I4,5-dichloro-7H-pyrrolor2,3-dlpyrimidine; N-Chlorosuccinimide (4.78 g, 35.81 mmol) was added portionwise to a stirred suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (5g, 32.56 mmol) in DCM, dry (125ml) at room temperature. The resulting suspension was stirred for 1 hour then heated to reflux for 5 hours, then allowed to cool down and left to stir at room temperature overnight. The reaction mixture was evaporated and suspended in water (50 mL). The suspension was filtered giving crude product as a grey solid. The solid was suspended in hot methnol and filtered. The solid was then suspended in hot ethyl acetate and filtered to give 4,5- dichloro-7H-pyrrolo[2,3-d]pyrimidine (4.87 g, 80 percent) as a grey solid. IH NMR (400.13 MHz, DMSO-d6) δ 7.91 (IH, s), 8.64 (IH, s), 12.87 (IH, s) MS m/e MH+ 188
72% With N-chloro-succinimide In dichloromethane at 20℃; for 18 h; METHOD I
4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (154 mg, 1.0 mmol) was suspended in 6.0 mL of dry dichloromethane in a flame-dried flask and to this mixture was added N-chlorosuccinimide (147 mg, 1.1 mmol) in one portion.
The resulting mixture stirred at room temperature for 18 h, at which time the solvent was removed under reduced pressure.
The residue was triturated with water and isolated by filtration to afford 137 mg (72percent) of the title compound as a gray solid, mp 224-227° C.(dec). LRMS: 188 (M+1).

Reference: [1] Synthesis, 2011, # 9, p. 1442 - 1446
[2] Archiv der Pharmazie, 2016, vol. 349, # 5, p. 356 - 362
[3] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 543 - 551
[4] Patent: CN107556318, 2018, A, . Location in patent: Paragraph 0101-0105
[5] Journal of Medicinal Chemistry, 1988, vol. 31, # 11, p. 2086 - 2092
[6] Patent: US2009/42893, 2009, A1, . Location in patent: Page/Page column 13
[7] Helvetica Chimica Acta, 1994, vol. 77, # 4, p. 897 - 903
[8] Patent: WO2008/75109, 2008, A1, . Location in patent: Page/Page column 115
[9] Patent: WO2008/75110, 2008, A1, . Location in patent: Page/Page column 107
[10] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 5, p. 2052 - 2062
[11] Patent: US6635762, 2003, B1, . Location in patent: Page/Page column 25
[12] Patent: US2009/264450, 2009, A1, . Location in patent: Page/Page column 7
[13] Patent: WO2012/80735, 2012, A1, . Location in patent: Page/Page column 11; 43
[14] Patent: WO2015/143712, 2015, A1, . Location in patent: Page/Page column 50; 51
  • 2
  • [ 1618-36-6 ]
  • [ 115093-90-8 ]
YieldReaction ConditionsOperation in experiment
83% With N-chloro-succinimide In dichloromethane at 43℃; for 8 h; A. Preparation of 4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidine; Following the procedure in Pdulo, J. S.; Saxena, N. K.; Nassiri, M. R.; Turk, S. R.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 31:2086 (1988), 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (Example 1A, 20. g, 0.13 mol) was suspended in anhydrous dichloromethane (500 mL), followed by addition of N-chlorosuccinimide (20.8 g, 0.160 mol). The reaction mixture was refluxed at 43° C. for 8 hours. The reaction was cooled down, and the white solid was filtered, washed with dichloromethane (300 mL), and dried to give 4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidine (20 g, 83percent)
Reference: [1] Patent: US2006/189638, 2006, A1, . Location in patent: Page/Page column 10
  • 3
  • [ 128-09-6 ]
  • [ 3680-69-1 ]
  • [ 115093-90-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 21, p. 6515 - 6518
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