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[ CAS No. 858956-25-9 ] {[proInfo.proName]}

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Chemical Structure| 858956-25-9
Chemical Structure| 858956-25-9
Structure of 858956-25-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 858956-25-9 ]

CAS No. :858956-25-9 MDL No. :MFCD19689702
Formula : C8H8N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :IKDLJHIRCTZDND-UHFFFAOYSA-N
M.W : 180.16 Pubchem ID :135547527
Synonyms :

Calculated chemistry of [ 858956-25-9 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.38
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 43.48
TPSA : 83.31 Ų

Pharmacokinetics

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) : -6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.15
Log Po/w (XLOGP3) : 0.62
Log Po/w (WLOGP) : 0.69
Log Po/w (MLOGP) : 0.06
Log Po/w (SILICOS-IT) : 0.75
Consensus Log Po/w : 0.65

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.56
Solubility : 4.99 mg/ml ; 0.0277 mol/l
Class : Very soluble
Log S (Ali) : -1.94
Solubility : 2.05 mg/ml ; 0.0114 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.05
Solubility : 16.1 mg/ml ; 0.0891 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.18

Safety of [ 858956-25-9 ]

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 [ 858956-25-9 ]

* 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.

  • Upstream synthesis route of [ 858956-25-9 ]
  • Downstream synthetic route of [ 858956-25-9 ]

[ 858956-25-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 57297-29-7 ]
  • [ 40876-98-0 ]
  • [ 858956-25-9 ]
YieldReaction ConditionsOperation in experiment
63%
Stage #1: for 0.333333 h;
Stage #2: at 70℃;
Stage #3: With hydrogenchloride In water at 20℃;
A solution of sodium hydroxide (2.85 g, 71.3 mmol) in water (3 ml) was added to a stirred solution of diethyl oxaloacetate sodium salt (8.7 g, 50 mmol) in water (50 ml) and the mixture stirred for 20 minutes. Cyclopropylcarboxamidine hydrochloride salt (5.0 g, 40 mmol) was added to the solution and the mixture was heated at 70 0C overnight, then cooled to ambient temperature and acidified to pH1 by the cautious addition of concentrated hydrochloric acid. The precipitate was isolated by filtration and dried to yield 2-cyclopropyl-4-hydroxypyrimidine-6-carboxylic acid (4.7 g, 63percent). Characterising data for the compound are as follows: 1H nmr (400MHz, d6-DMSO) δH 13.30 (1H, br s), 12.97 (1H, br s), 6.59 (1H, s), 1.94 (1H, quintet), 1.04 (4H, m) ppm.
63%
Stage #1: With sodium hydroxide In water for 0.333333 h;
Stage #2: at 70℃;
Stage #3: With hydrogenchloride In water at 20℃;
A solution of sodium hydroxide (2.85 g, 71.3 mmol) in water (3 ml) was added to a stirred solution of diethyl oxaloacetate sodium salt (8.7 g, 50 mmol) in water (50 ml) and the mixture stirred for 20 minutes. Cyclopropylcarboxamidine hydrochloride salt (5.0 g, 40 mmol) was added to the solution and the mixture was heated at 70 0C overnight, then cooled to ambient temperature and acidified to pH1 by the cautious addition of concentrated hydrochloric acid. The precipitate was isolated by filtration and dried to yield 2-cyclopropyl-4-hydroxypyrimidine-6-carboxylic acid (4.7 g, 63percent). 1H nmr (400MHz, d6-DMSO) δH 13.30 (1 H, br s), 12.97 (1 H, br s), 6.59 (1 H, s), 1.94 (1 H, quintet), 1.04 (4H, m) ppm.
Reference: [1] Patent: WO2009/81112, 2009, A2, . Location in patent: Page/Page column 114
[2] Patent: WO2010/92339, 2010, A1, . Location in patent: Page/Page column 83-84
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