[ CAS No. 75893-75-3 ]

Name: 75893-75-3|6-Cyclopropylnicotinic acid|95%
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Quality Control of [ 75893-75-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 75893-75-3 ]

CAS No. :	75893-75-3	MDL No. :	MFCD18255573
Formula :	C₉H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	163.17 g/mol	Pubchem ID :	12440058
Synonyms :

Calculated chemistry of of [ 75893-75-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.66
TPSA :	50.19 Å²

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) :	-6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.44
Log Po/w (XLOGP3) :	0.95
Log Po/w (WLOGP) :	1.59
Log Po/w (MLOGP) :	-0.13
Log Po/w (SILICOS-IT) :	1.75
Consensus Log Po/w :	1.12

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.69
Solubility :	3.35 mg/ml ; 0.0205 mol/l
Class :	Very soluble
Log S (Ali) :	-1.59
Solubility :	4.18 mg/ml ; 0.0256 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.99
Solubility :	1.68 mg/ml ; 0.0103 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.55

Safety of [ 75893-75-3 ]

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 [ 75893-75-3 ]

* 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.

Downstream synthetic route of [ 75893-75-3 ]

[ 75893-75-3 ] Synthesis Path-Downstream 1~7

1
4-phenyldecahydroquinolin-4-ol [ No CAS ]
[ 75893-75-3 ]
C₂₄H₂₈N₂O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2359 - 2364

Yield	Reaction Conditions	Operation in experiment
	With water; sodium hydroxide; In ethanol; for 20.0h;Reflux;	General procedure: Intermediate 6A: 5-Iso ropyl-3-methyI-lH-pyrazole-4-carboxylic acidEthyl 5-isopropyl-3-methyl-lH-pyrazole-4-carboxylate (WO2009/013211) (2.1 g, 10.7 mmol) was dissolved in ethanohwater (2:1, 10 mL), to it was added sodium hydroxide (857 mg, 21.4 mmol) and refluxed for 20 h. Volatiles were evaporated under reduced pressure. Aqueous layer was diluted with water (20 mL) and extracted with ethyl acetate (2 X 20 mL). Combined organic layer was washed with brine (25 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give 750 mg (73%) of 5 -isopropyl-3 -methyl- 1H- pyrazole-4-carboxylic acid.? NMR (400 MHz, CDCI3): delta 1.17 (d, J = 6.9 Hz, 6H), 2.32 (s, 3H), 3.45-3.54 (m, 1H), 12.23 (brs, 2H). MS (ES) m/z 169.1 (M+l).
	With sodium hydroxide; In ethanol; water; for 20.0h;Reflux;	General procedure: Intermediate 6A: 5-Isopropyl-3-methyl-1H-pyrazole-4-carboxylic acid Ethyl 5-isopropyl-3-methyl-1H-pyrazole-4-carboxylate (WO2009/013211) (2.1 g, 10.7 mmol) was dissolved in ethanol:water (2:1, 10 mL), to it was added sodium hydroxide (857 mg, 21.4 mmol) and refluxed for 20 h. Volatiles were evaporated under reduced pressure. Aqueous layer was diluted with water (20 mL) and extracted with ethyl acetate (2*20 mL). Combined organic layer was washed with brine (25 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give 750 mg (73%) of 5-isopropyl-3-methyl-1H-pyrazole-4-carboxylic acid. 1H NMR (400 MHz, CDCl3): delta 1.17 (d, J=6.9 Hz, 6H), 2.32 (s, 3H), 3.45-3.54 (m, 1H), 12.23 (brs, 2H). MS (ES) m/z 169.1 (M+1).

3
[ 1147531-04-1 ]
[ 75893-75-3 ]
N-[2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-6-cyclopropyl-pyridine-3-carboxamide [ No CAS ]

Reference： [1]Patent: WO2013/157021,2013,A1

4
[ 1147531-04-1 ]
[ 75893-75-3 ]
N-[3-bromo-2-[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]-6-cyclopropylpyridine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20.0℃; for 16.0h;	Step-6: Synthesis of N-[3-bromo-2-[[tert-butyI(dimethyl)siIyl]oxymethyl]phenyl]-6- cyclopropyl-pyridine-3-carboxamide: To a solution of <strong>[75893-75-3]6-cyclopropylpyridine-3-carboxylic acid</strong> (0.5 g, 3.06 mmol), 3-bromo-2-[[tert- butyl(dimethyl)silyl]oxymethyl]aniline (1.16 g, 3.67 mmol) and HOBt (0.495 g, 3.67 mmol) in DCM (15 mL) was added NMM (0.5 mL, 4-59 mmol) and EDCI.HCl (0.876 g, 4.59 mmol). The reaction mixture was stirred at room temperature for 16 h. After completion of the reaction (as indicated by TLC), water (10 mL) was added to it and extraction was carried out using DCM (50 mL x 2). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue was purified using column chromatography (Si02, 10% ethyl acetate in hexanes) to afford title compound (0.5 g, 35%). LCMS: m/z 461.2 (M + 1)+. NMR (400 MHz, CDC13) delta 0.15 (s, 6H), 0.87 (s, 9H), 1.05-1.10 (m, 2H), 1.1 1-1.51 (m, 2H), 2.06-2.16 (m, 1H), 5.1 1 (s, 2H), 7.19-7.23 (aromatics, 2H), 7.33 (d, J = 8.0 Hz, 1H), 8.03 (dd, J = 8.0, 2.0 Hz, 1H), 8.33 (d, J = 8.0 Hz, 1H), 8.99 (d, J = 2.0 Hz, lH), 9.99 (s, lH).

Reference： [1]Patent: WO2013/157021,2013,A1 .Location in patent: Page/Page column 51-52

5
[ 75893-75-3 ]
2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]benzylamine [ No CAS ]
6-cyclopropyl-N-([2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methyl)pyridine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20.0℃; for 16.0h;Inert atmosphere;	Example 56 6-Cyclopropyl-N-([2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methyl)pyridine-3-carboxamide (56) In a 10-mL round bottom flask purged and maintained with an inert atmosphere of nitrogen, [2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methanamine (100 mg, 0.31 mmol, 1.00 equiv) and <strong>[75893-75-3]6-cyclopropylpyridine-3-carboxylic acid</strong> (60.7 mg, 0.37 mmol, 1.20 equiv) were dissolved in N,N-dimethylformamide (2 mL), to which were added HATU (176.9 mg, 0.47 mmol, 1.50 equiv) and DIEA (120.3 mg, 0.93 mmol, 3.00 equiv) in sequence at room temperature. The resulting solution was stirred for 16 h at room temperature. When the reaction was done, it was quenched by the addition of 5 mL water and the mixture was extracted with dichloromethane (310 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by prep-HPLC using the following conditions: column, X Bridge C18, 19150 mm, 5 um; mobile phase, acetonitrile in water (with 0.05% TFA), 30% to 70% gradient in 10 min; detector, UV, 254 nm. 6-cyclopropyl-N-([2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methyl)pyridine-3-carboxamide (20 mg, 13%) was obtained as white solid. HPLC: 97.7% purity. MS: m/z=468.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 6 13.39 (br s, 1H), 9.20-9.17 (m, 1H), 8.91 (d, J=2.0 Hz, 1H), 8.44 (s, 1H), 8.29-8.20 (m, 2H), 8.14-8.11 (m, 3H), 7.56-7.52 (m, 2H), 7.42 (d, J=8.0 Hz, 1H), 4.60 (s, 2H), 3.94 (s, 3H), 2.33-2.15 (m, 1H), 1.05-1.01 (m, 4H).

Reference： [1]Patent: US2016/96834,2016,A1 .Location in patent: Paragraph 0399-0400

6
[ 75893-75-3 ]
5-[(2R,3R)-3-amino-2-methylpiperidin-1-yl]-3-[4-(oxan-4-yloxy)phenyl]amino}pyrazine-2-carbonitrile [ No CAS ]
N-[(2R,3R)-1-(5-cyano-6-[4-(oxan-4-yloxy)phenyl]amino}pyrazin-2-yl)-2-methylpiperidin-3-yl]-6-cyclopropylpyridine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20.0℃; for 1.0h;	5-[(2R,3R)-3-amino-2-methylpiperidin-1-yl]-3-[4-(oxan-4-yloxy)phenyl]amino}pyrazine-2- carbonitrile (102.8 mg, 0.25 mmol) was dissolved in DMF (4 mL), <strong>[75893-75-3]6-cyclopropylnicotinic acid</strong> (62 mg, 0.38 mmol), DIPEA (0.2 mL, 1.26 mmol) and PyBOP (196 mg, 0.38 mmol) were added. The mixture was stirred at room temperature 1 h. Water and DCM were added and the mixture was extracted with DCM. The organic phase was dried over Na2SO4, filtered and evaporated to give a crude which was purified by silica flash chromatography with 50% to 100% ethyl acetate in cyclohexane to afford N-[(2R,3R)-1-(5-cyano-6-[4-(oxan-4-yloxy)phenyl]amino}pyrazin-2- yl)-2-methylpiperidin-3-yl]-6-cyclopropylpyridine-3-carboxamide (120.7 mg, 87% yield) as a yellow solid. MS found for C31H35N7O3 as (M+H)+ 554.0.

Reference： [1]Patent: WO2016/196776,2016,A2 .Location in patent: Paragraph 001244

7
[ 75893-75-3 ]
5-[(2R,3R)-3-amino-2-methylpiperidin-1-yl]-3-[4-(oxan-4-yloxy)phenyl]amino}pyrazine-2-carbonitrile [ No CAS ]
5-[(2R,3R)-3-(6-cyclopropylpyridine-3-amido)-2-methylpiperidin-1-yl]-3-[4-(oxan-4-yloxy)phenyl]amino}pyrazine-2-carboxamide [ No CAS ]

Reference： [1]Patent: WO2016/196776,2016,A2

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[ 75893-75-3 ]

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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 75893-75-3 ]

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[ 75893-75-3 ] Synthesis Path-Downstream 1~7

Related Functional Groups of [ 75893-75-3 ]

Carboxylic Acids

Related Parent Nucleus of [ 75893-75-3 ]

Pyridines

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[ 75893-75-3 ]

Related Parent Nucleus of
[ 75893-75-3 ]