[ CAS No. 862695-75-8 ] {[proInfo.proName]}

Name: 862695-75-8|6-Chloro-2-cyclopropylnicotinic acid|95+%
Brand: Ambeed
SKU: A280284
Rating: 95 (29 reviews)

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Quality Control of [ 862695-75-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 862695-75-8 ]

SDS Specification

Alternatived Products of [ 862695-75-8 ]

Product Details of [ 862695-75-8 ]

CAS No. :	862695-75-8	MDL No. :	MFCD18255903
Formula :	C₉H₈ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FZPUPGGRIJXKTC-UHFFFAOYSA-N
M.W :	197.62	Pubchem ID :	59842342
Synonyms :

Calculated chemistry of [ 862695-75-8 ]

Physicochemical Properties

Num. heavy atoms :	13
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 :	48.67
TPSA :	50.19 Å²

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) :	-6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.61
Log Po/w (XLOGP3) :	1.92
Log Po/w (WLOGP) :	2.25
Log Po/w (MLOGP) :	0.44
Log Po/w (SILICOS-IT) :	2.37
Consensus Log Po/w :	1.72

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.48
Solubility :	0.648 mg/ml ; 0.00328 mol/l
Class :	Soluble
Log S (Ali) :	-2.6
Solubility :	0.499 mg/ml ; 0.00253 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.62
Solubility :	0.476 mg/ml ; 0.00241 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.96

Safety of [ 862695-75-8 ]

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 [ 862695-75-8 ]

* 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 [ 862695-75-8 ]
Downstream synthetic route of [ 862695-75-8 ]

[ 862695-75-8 ] Synthesis Path-Upstream 1~5

1
[ 862695-74-7 ]
[ 862695-75-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6756 - 6761
[2] Patent: WO2005/75464, 2005, A1, . Location in patent: Page/Page column 25
[3] Patent: WO2005/80342, 2005, A1, . Location in patent: Page/Page column 35

2
[ 32249-35-7 ]
[ 862695-75-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6756 - 6761

3
[ 862695-71-4 ]
[ 862695-75-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6756 - 6761

4
[ 862695-72-5 ]
[ 862695-75-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6756 - 6761

5
[ 862695-73-6 ]
[ 862695-75-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6756 - 6761

[ 862695-75-8 ] Synthesis Path-Downstream 1~8

1
[ 862695-74-7 ]
[ 862695-75-8 ]

Yield	Reaction Conditions	Operation in experiment
		Description 13: 6-Chloro-2-cyclopropyl-nicotinic acid; To 6-chloro-2-cyclopropyl-nicotinic acid methyl ester (Description 12) (1.23g) was added tetrahydrofuran (9ml) and water (3ml) followed by lithium hydroxide (0.72g). The mixture was stirred vigorously at room temperature overnight, and then evaporated under reduced pressure. To the residue was added water (50ml), which was then acidified to pHl using conc. HCL. The white precipitate that formed was filtered and washed with water (50ml) and dried to afford the title compound (lg) NMR (DMSO) 8 0.95-1. 09 (4H, m), 3.03-3. 12 (1H, m), 7.31 (1H, d), 8.12 (1H, s), 13.50 (1H, s). LC/MS t= 2. 58 min, wiz = 198 consistent with molecular formula C9H8CINO2
		Intermediate 28: 6-Chloro-2-cyclopropyl-nicotinic acid; To 6-chloro-2-cyclopropyl-nicotinic acid methyl ester (1.23g) was added tetrahydrofuran (9ml) and water (3ml) followed by lithium hydroxide (0.72g). The mixture was stirred vigorously at room temperature overnight, and then evaporated under reduced pressure. To the residue was added water (50ml), which was then acidified to pHl using conc. hydrochloric acid. The white precipitate that formed was filtered and washed with water (50ml) and dried to afford the title compound (lg) NMR (DMSO) 8 0.95-1. 09 (4H, m), 3.03-3. 12 (1H, m), 7.31 (1H, d), 8.12 (1H, s), 13.50 (1H, s). LC/MS t= 2. 58 min, [MH+] = 198 consistent with molecular formula C9H8CIN02

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6756 - 6761
[2]Patent: WO2005/75464,2005,A1 .Location in patent: Page/Page column 25
[3]Patent: WO2005/80342,2005,A1 .Location in patent: Page/Page column 35

2
[ 130290-79-8 ]
[ 862695-75-8 ]
[ 862695-76-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethylmorpholine;; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 20.0℃;	Description 14: 6-Chloro-2-cyclopropyl-N- (tetrahydro-pyran-4-ylmethyl)-nicotinamide; To a solution of <strong>[862695-75-8]6-chloro-2-cyclopropyl-nicotinic acid</strong> (Description 13) (2. 1g) in dimethylformamide (20ml) was added 1-hydroxybenzotriazole (730mg), 1- [3- (dimethylamino) propyl] -3-ethylcarbodiimide hydrochloride (2. 31 g), N-ethyl morpholine (3. 2ml) followed by (tetrahydro-pyran-4-yl) -methylamine (1.9g). The mixture was stirred at room temperature overnight. Water (100ml) was added and the mixture was extracted with ethyl acetate (2x 100ml). The combined organic layers were washed with 10% sodium hydrogen carbonate (100ml), and brine (50ml). The dried (Na2SO4) organic layer was evaporated under reduced pressure. The residue was purified by Biotage chromatography over silica using ethyl acetate (60%) /isohexane (40%) to give the title compound (2. 81g) as a white solid. NMR (MeOD) b 0.96-1. 10 (4H, m), 1.28-1. 41 (2H, m), 1.65-1. 73 (2H, m), 1.80-1. 94 (1H, m), 2.24-2. 33 (1H, m), 3.24-3. 29 (2H, m), 3.37-3. 47 (2H, m), 3. 92-4.00 (2H, m), 7.16 (1H, d), 7.6 2 (1H, d). LC/MS t= 2. 39 min, molecular ion observed [MH] = 295 consistent with molecular formula C15H19ClN2O2
	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 20.0℃;	Intermediate 29: 6-Chloro-2-cyclopropyl-N- (tetrahydro-pyran-4-ylmethyl)-nicotinamide; To a solution of <strong>[862695-75-8]6-chloro-2-cyclopropyl-nicotinic acid</strong> (2. 1g) in dimethylformamide (20ml) was added 1-hydroxybenzotriazole (730mg), 1- [3- (dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride (2. 3 1 g), N-ethyl morpholine (3. 2ml) followed by (tetrahydro-pyran-4-yl)- methylamine (1.9g). The mixture was stirred at room temperature overnight. Water (100ml) was added and the mixture was extracted with ethyl acetate (2x 100ml). The combined organic layers were washed with 10% sodium hydrogen carbonate (100ml), and brine (50ml). The dried (Na2S04) organic layer was evaporated under reduced pressure. The residue was purified by Biotage chromatography over silica using ethyl acetate (60%) /isohexane (40%) to give the title compound (2. 81g) as a white solid. NMR (MeOD) 8 0.96-1. 10 (4H, m), 1. 28-1. 41 (2H, m), 1.65-1. 73 (2H, m), 1.80-1. 94 (1H, m), 2. 24-2. 33 ( H, m) ; 3.24-3. 29 (2H, m), 3 37 - 3. 47 (2H, m), 3.92-4. 00 (2H, m), 7.16 (1H, d), 7. 6 2 (1H, d). LC/MS t= 2. 39 min, molecular ion observed [MH] = 295 consistent with molecular formula C15Hl9CIN202

Reference： [1]Patent: WO2005/75464,2005,A1 .Location in patent: Page/Page column 25-26
[2]Patent: WO2005/80342,2005,A1 .Location in patent: Page/Page column 35-36

3
[ 32249-35-7 ]
[ 862695-75-8 ]