[ CAS No. 298708-79-9 ] {[proInfo.proName]}

Name: 298708-79-9|Methyl 4-(2-chloro-4-fluorophenyl)-2-(3,5-difluoropyridin-2-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate|98%
Brand: Ambeed
SKU: A127980
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2D 3D

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Quality Control of [ 298708-79-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 298708-79-9 ]

SDS Specification

Alternatived Products of [ 298708-79-9 ]

Product Details of [ 298708-79-9 ]

CAS No. :	298708-79-9	MDL No. :	MFCD30729326
Formula :	C₁₈H₁₃ClF₃N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FVNJBPMQWSIGJK-UHFFFAOYSA-N
M.W :	395.76	Pubchem ID :	9865484
Synonyms :	(±)-BAY 41-4109;BAY41-4109 Racemic

Calculated chemistry of [ 298708-79-9 ]

Physicochemical Properties

Num. heavy atoms :	27
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.17
Num. rotatable bonds :	4
Num. H-bond acceptors :	7.0
Num. H-bond donors :	1.0
Molar Refractivity :	99.84
TPSA :	63.58 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.01
Log Po/w (XLOGP3) :	3.11
Log Po/w (WLOGP) :	3.87
Log Po/w (MLOGP) :	3.75
Log Po/w (SILICOS-IT) :	5.27
Consensus Log Po/w :	3.8

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.32
Solubility :	0.019 mg/ml ; 0.0000481 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.11
Solubility :	0.0305 mg/ml ; 0.000077 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-7.32
Solubility :	0.000019 mg/ml ; 0.000000048 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.14

Safety of [ 298708-79-9 ]

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 [ 298708-79-9 ]

* 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 [ 298708-79-9 ]
Downstream synthetic route of [ 298708-79-9 ]

[ 298708-79-9 ] Synthesis Path-Upstream 1~3

1
[ 298709-35-0 ]
[ 298709-32-7 ]
[ 298708-79-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium acetate In isopropyl alcohol for 4 h; Heating / reflux	[0193] 4.5 g (23.2 mmol) of 3,5-difluoro-2-pyridinecarboximidamide hydrochloride from Example VI and 7.7 g (30 mmol) of methyl 2-acetyl-3-(2-chloro-4-fluorophenyl)-2-propenoate from Example VII and 2.3 g (27.9 mmol) of sodium acetate are dissolved or suspended in 120 ml of isopropanol and boiled under reflux for 4 hours. Cooling to room temperature is followed by filtration with suction to remove inorganic salts, and concentration. The residue is taken up in a mixture of 30 ml of 1N hydrochloric acid and 35 ml of ethyl acetate, and the phases are separated. The ethyl acetate phase is back-extracted once with 30 ml of 1N hydrochloric acid. The combined aqueous phases are extracted three times with 10 ml of diethyl ether each time. The aqueous phase is made alkaline with NaOH and extracted with ethyl acetate. The organic phases are dried over sodium sulfate and concentrated. [0194] 7.4 g (80percent) of product are obtained [0195] Melting point: 126° C. [0196] 1H-NMR (DMSO-D6): 2.4 (s, 3H) ppm, 3.5 (s, 3H) ppm, 6.0 (s, 1H) ppm, 7.2 (m, 1H) ppm, 7.4 (m, 2H) ppm, 8.0 (m, 1H) ppm, 8.55 (d, J=2 Hz, 1H) ppm, 9.75 (s, NH) ppm. [0197] The (-)-enantiomer is obtained after separation of the enantiomers on chiral columns (Chiralpak AS from Baker, mobile phase n-heptane/ethanol=8:2). [0198] Melting pont: 117° C. (from ethanol) [0199] [α]D20: -62.8° (methanol)

Reference： [1] Patent: US2003/232842, 2003, A1, . Location in patent: Page 10

2
[ 298709-29-2 ]
[ 298708-79-9 ]

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 8, p. 3352 - 3371

3
[ 298709-32-7 ]
[ 84194-36-5 ]
[ 105-45-3 ]
[ 298708-79-9 ]

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 8, p. 3352 - 3371

[ 298708-79-9 ] Synthesis Path-Downstream 1~6

1
[ 298709-35-0 ]
[ 298709-32-7 ]
[ 298708-79-9 ]
C₁₈H₁₃ClF₃N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium acetate; In isopropyl alcohol; for 4.0h;Heating / reflux;	[0193] 4.5 g (23.2 mmol) of 3,5-difluoro-2-pyridinecarboximidamide hydrochloride from Example VI and 7.7 g (30 mmol) of methyl 2-acetyl-3-(2-chloro-4-fluorophenyl)-2-propenoate from Example VII and 2.3 g (27.9 mmol) of sodium acetate are dissolved or suspended in 120 ml of isopropanol and boiled under reflux for 4 hours. Cooling to room temperature is followed by filtration with suction to remove inorganic salts, and concentration. The residue is taken up in a mixture of 30 ml of 1N hydrochloric acid and 35 ml of ethyl acetate, and the phases are separated. The ethyl acetate phase is back-extracted once with 30 ml of 1N hydrochloric acid. The combined aqueous phases are extracted three times with 10 ml of diethyl ether each time. The aqueous phase is made alkaline with NaOH and extracted with ethyl acetate. The organic phases are dried over sodium sulfate and concentrated. [0194] 7.4 g (80%) of product are obtained [0195] Melting point: 126 C. [0196] 1H-NMR (DMSO-D6): 2.4 (s, 3H) ppm, 3.5 (s, 3H) ppm, 6.0 (s, 1H) ppm, 7.2 (m, 1H) ppm, 7.4 (m, 2H) ppm, 8.0 (m, 1H) ppm, 8.55 (d, J=2 Hz, 1H) ppm, 9.75 (s, NH) ppm. [0197] The (-)-enantiomer is obtained after separation of the enantiomers on chiral columns (Chiralpak AS from Baker, mobile phase n-heptane/ethanol=8:2). [0198] Melting pont: 117 C. (from ethanol) [0199] [alpha]D20: -62.8 (methanol)

Reference： [1]Patent: US2003/232842,2003,A1 .Location in patent: Page 10

2
[ 298709-32-7 ]
[ 84194-36-5 ]
[ 105-45-3 ]
[ 298708-79-9 ]