[ CAS No. 113118-82-4 ] {[proInfo.proName]}

Name: 113118-82-4|5-Chloronicotinaldehyde|97%
Brand: Ambeed
SKU: A382554
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Quality Control of [ 113118-82-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 113118-82-4 ]

CAS No. :	113118-82-4	MDL No. :	MFCD08457773
Formula :	C₆H₄ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BCELHNLIYYAOLV-UHFFFAOYSA-N
M.W :	141.56	Pubchem ID :	14444196
Synonyms :

Calculated chemistry of [ 113118-82-4 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	34.63
TPSA :	29.96 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) :	-6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.26
Log Po/w (XLOGP3) :	0.94
Log Po/w (WLOGP) :	1.55
Log Po/w (MLOGP) :	0.4
Log Po/w (SILICOS-IT) :	2.16
Consensus Log Po/w :	1.26

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.74
Solubility :	2.59 mg/ml ; 0.0183 mol/l
Class :	Very soluble
Log S (Ali) :	-1.16
Solubility :	9.89 mg/ml ; 0.0699 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.56
Solubility :	0.387 mg/ml ; 0.00274 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.21

Safety of [ 113118-82-4 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P280-P301+P310-P305+P351+P338	UN#:	2811
Hazard Statements:	H301-H317-H319	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 113118-82-4 ]

* 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 [ 113118-82-4 ]

[ 113118-82-4 ] Synthesis Path-Downstream 1~40

1
[ 85320-79-2 ]
[ 113118-82-4 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1933,vol. <2> 138,p. 244,257

2
[ 462-94-2 ]
[ 113118-82-4 ]
<i>N</i>-(5-chloro-[3]pyridylmethyl)-pentanediyldiamine [ No CAS ]

Reference： [1]Patent: US2317757,1941,

3
[ 141-82-2 ]
[ 113118-82-4 ]
[ 118419-97-9 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 583 - 593

4
[ 113118-73-3 ]
[ 113118-82-4 ]

Reference： [1]Heterocycles,1987,vol. 26,p. 2159 - 2164

5
[ 118420-18-1 ]
[ 113118-82-4 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 583 - 593

6
[ 117830-18-9 ]
[ 113118-82-4 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 583 - 593

7
[ 113118-82-4 ]
[ 118420-36-3 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 583 - 593

8
[ 20825-98-3 ]
[ 113118-82-4 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 583 - 593

9
[ 626-60-8 ]
[ 113118-82-4 ]

Reference： [1]Heterocycles,1987,vol. 26,p. 2159 - 2164

10
[ 113118-67-5 ]
[ 113118-82-4 ]

Reference： [1]Heterocycles,1987,vol. 26,p. 2159 - 2164

11
[ 22620-27-5 ]
[ 113118-82-4 ]

Yield	Reaction Conditions	Operation in experiment
27%		EXAMPLE 7; 2-Amino-4-(5-chloro-pyridin-3-yl)-3-cyano-7-methyl-4H-pyrrolo[2,3-h]chromene; a) 5-Chloro-pyridine-3-carbaldehyde:; To a solution of oxalyl chloride (2.0 M solution in CH2Cl2, 30.0 mL, 60.0 mmol) in anhydrous CH2Cl2 (20.0 mL) cooled at 0 C., was added anhydrous DMF (3.0 mL, 38 mmol) dropwise, resulting in a white precipitate. The ice bath was removed and the white suspension was allowed to warm to room temperature. The white precipitate was filtered and collected on a sintered glass funnel. To a suspension of the above white precipitate (0.487 g, 3.81 mmol) in anhydrous acetonitrile (5.86 mL) and anhydrous THF (11.91 mL) at -55 C. was added pyridine (0.043 mL, 0.53 mmol) and 5-chloronicotinic acid (0.200 g, 1.27 mmol). The white suspension was warmed to room temperature over the next 3 h and then cooled to -78 C. While maintaining the internal temperature below -70 C., CuI (0.010 g) was added followed by the dropwise addition of LiAlH(t-BuO)3 (1.0 M solution in THF, 0.646 g, 2.54 mmol). The internal temperature was maintained below -70 C. for an additional 0.5 h and then the reaction was quenched with 2.0 N HCl (3 mL). The suspension was warmed to room temperature and diluted with ethyl acetate (150 mL), dried over Na2SO4, filtered through sintered glass and concentrated to a brown residue. The residue was purified by column chromatography (elution with EtOAC:hexanes, 1:4), and yielded 0.0484 g (27%) of the title compound as a white solid. 1H NMR (CDCl3): 10.11 (s, 1H), 8.95 (d, J=1.93 Hz, 1H), 8.81 (d, J=2.47 Hz, 1H), 8.15 (dd, J=2.47, 1.93 Hz, 1H).

Reference： [1]Patent: US2006/104998,2006,A1 .Location in patent: Page/Page column 18

12
N-cyclopropylguanidine hydrochloride [ No CAS ]
[ 113118-82-4 ]
[ 105-56-6 ]
[ 945002-16-4 ]

Yield	Reaction Conditions	Operation in experiment
26%	With potassium carbonate; In ethanol; at 75℃; for 18h;	3-Chloro-5-formylpyridine (0.50 g, 3.57 mmol), ethylcyanoacetate (0.40 g, 3.57 ramol), N- cyclopropylguanidine.HCl (0.48 g, 3.57 mmol), and potassium carbonate (0.54 g, 3.92 mmol) was stirred in ethanol (20 mL) at 75 0C for 18 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated and concentrated to give a residue which was purified using flash chromatography (100% EtOAc) to give 5-cyano-4-(3- chloro-5-pyridyl)-2-cydopropylamino-6-oxopyrimidine (0.26 g, 26%). MS m/z calculated for (M + H)+ 287, found 287.

Reference： [1]Patent: WO2007/84560,2007,A2 .Location in patent: Page/Page column 161

13
[ 1022157-73-8 ]
[ 113118-82-4 ]
[ 1022156-49-5 ]

Yield	Reaction Conditions	Operation in experiment
16%	With triethylamine; In methanol; at 20℃;	5.1.96 EXAMPLE 96: SYNTHESIS OF 2-(5-CHLOROPYRIDIN- 3-YL)-8-OXO-9-(2-(TRIFLUOROMETHYL)PHENYL)-8,9-DIHYDRO-7H-PURINE-6-CARBOXAMIDE; EPO <DP n="136"/>[00432] A. Z-CS-Chloropyridin-S-yO-S-oxo^-CZ^trifluoromethyOphenyO-S^- dihydro-7H-purine-6-carboxamide. (Z)-l-(2-Amino-l ,2-dicyanovinyl)-3-(2- (trifluoromethyl)phenyl)urea {See Example 50.A) (0.15 g, 0.51 mmol), 5- chloronicotinaldehyde (0.14 g, 0.99 mmol), and triethylamine (0.10 ml, 0.72 mmol) were combined in methanol (7.0 mL) and stirred at room temperature overnight. Excess solvent was removed under reduced pressure and the resulting residue was purified by reverse-phase preparatory HPLC (30-80% acetonitrile + 0.1% TFA in H2O + 0.1% TFA, over 30 min). Clean fractions were neutralized with ammonium hydroxide and solvent removed under reduced pressure. The resulting material was taken up in ethyl acetate, washed successively with potassium carbonate, water, and brine. The solution was dried over sodium sulfate, filtered and solvent removed under reduced pressure to provide the product as an off white solid (0.035 g, 0.08 mmol, 16% yield). 1H NMR (400 MHz, DMSO-^5) delta 12.07 (bs, IH), 9.23 (s, IH), 8.95 (s, IH), 8.59 (m, 2H), 7.93 (m, 2H), 7.78 (m, 2H), 7.63 (bs, IH); MS (ESI) m/z 435.0 [M+l]+; mp 230-2320C.

Reference： [1]Patent: WO2008/51494,2008,A1 .Location in patent: Page/Page column 134-135

14
[ 1062205-68-8 ]
[ 113118-82-4 ]
[ 1208308-08-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 653 - 656

15
[ 113118-82-4 ]
[ 1530-45-6 ]
ethyl (2E)-3-(5-chloropyridin-3-yl)prop-2-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%		NaH (570 mg, 14.24 mmol) was added portion wise to stirred anhydrous DMSO (10 ml_). The mixture was heated to 80C until evolution of gas ceased and then cooled to 0C. A solution of (carbethoxymethyl)- triphenylphosphonium bromide (3.05 g, 7.12 mmol) in DMSO (10 ml_) was then added and the mixture stirred at r.t for 30 min. The mixture was cooled to 0C and a solution of <strong>[113118-82-4]5-chloronicotinaldehyde</strong> (1 .0 g, 7.12 mmol) in DMSO (10 ml_) was added and the mixture was stirred at r.t for 1 h. The mixture was then poured into aqueous 1 M HCI and extracted into DCM (3 x 50 ml_). The organics were combined and washed with H2O (3 x 100 ml_) and brine (3 x 100 ml_), separated, dried (MgSO ) and concentrated. Purification by flash silica column chromatography (gradient elution /'-hex to 25% EtOAc in /-hex) gave the title compound as a yellow solid (1 .1 g, 57%). LCMS (ES+) 271 (M+H)+.

Reference： [1]Patent: WO2012/103008,2012,A1 .Location in patent: Page/Page column 130

16
[ 113118-82-4 ]
[ 1250695-64-7 ]
[ 1440251-71-7 ]

Yield	Reaction Conditions	Operation in experiment
22%		General procedure: To each reaction tube in a 24-position Bohdan MiniBlock XT was added the appropriate aldehyde (5.0 equiv, 1.15 mmol), which was dissolved in MeCN (1 mL). A solution of 2-(benzo[d][1,3]dioxol-5- yl)pyrimidin-4-amine (8) in MeCN (0.13 M, 1.8 mL, 0.23 mmol, 1.0 equiv) was then dispensed into each tube. ClTi(Oi-Pr)3 (95%, 0.35 mL, 1.38 mmol, 6.0 equiv) was added to each tube, followed by AcOH (3 drops). The reactions were shaken at 450 rpm for 5 minutes, and then solid NaBH(OAc)3 (95%, 257 mg, 1.15 mmol, 5.0 equiv) was added to each tube. The reactions were shaken at 450 rpm for an additional 1.5 hours, and then a solution of 15% aqueous NH4OH (2 mL) and CH2Cl2 (2 mL) were added to each tube causing white solids to precipitate. Shaking was continued for 30 minutes at 450 rpm. Using stackable 24-position Bohdan MiniBlock XTs, the liquid portions of the crude reaction mixtures were passed into phase separators, to which H2O (2 mL) was added. The biphasic mixtures were mixed by hand using pipettes, and then the heavier organic layers were passed from the phase separators into new reaction tubes. The white solids in the original reaction tubes were washed with CH2Cl2 (2 mL) and the washings were passed into the closed phase separators. The biphasic mixtures were again mixed by hand using pipettes and the heavier organic layers were passed into the reaction tubes containing the organic layers from the first separation. The crude reaction mixtures were then placed on a sample concentrator to remove the solvents. TFA/MeOH (1:19, 3 mL) was added to each crude reaction mixture, and the samples were then shaken at 450 rpm for 1 hour. The solutions were then passed onto columns of Dowex 50WX4-400 ion exchange resin (2.0 g, pre-washed with TFA/MeOH (1:99, 5 mL)). Each reaction tube was washed with MeOH (2 mL) and the washings were allowed to pass onto the Dowex columns. The columns were washed with MeOH (3 mL) and the washings discarded. The products were then eluted into collection tubes using a mixture of Et3N/MeOH (1:9, 10 mL). Solvents were removed using a sample concentrator and the products were subjected to reverse-phase preparative HPLC purification.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3654 - 3661

17
[ 113118-82-4 ]
[ 928064-55-5 ]

Yield	Reaction Conditions	Operation in experiment
2.1 g	With hydroxylamine hydrochloride; sodium acetate; In ethanol; at 30℃; for 2.25h;Inert atmosphere;	Hydroxylamine hydrochloride (2.3 g) and sodium acetate (2.7 g) were initially charged in ethanol (50 ml) under nitrogen (white suspension). 5-Chloronicotinaldehyde (4.3 g) were dissolved in ethanol (120 ml) (30 C., ultrasound bath) and added dropwise thereto within 15 minutes. The reaction mixture was stirred for 2 hours and concentrated at 40 C. Dichloromethane (550 ml) and water (250 ml) were added and the resulting precipitate is filtered off and dried. Yield: 2.1 g of <strong>[113118-82-4]5-chloronicotinaldehyde</strong> oxime

Reference： [1]Patent: US2015/223461,2015,A1 .Location in patent: Paragraph 0256

18
[ 113118-82-4 ]
ethyl 3-(5-chloropyridin-3-yl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate [ No CAS ]

Reference： [1]Patent: US2015/223461,2015,A1

19
[ 113118-82-4 ]
3-(5-chloropyridin-3-yl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid [ No CAS ]

Reference： [1]Patent: US2015/223461,2015,A1

20
[ 113118-82-4 ]
3-(5-chloropyridin-3-yl)-N-isopropyl-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxamide [ No CAS ]

Reference： [1]Patent: US2015/223461,2015,A1

21
[ 113118-82-4 ]
3-(5-chloropyridin-3-yl)-N-isopropyl-5-methyl-4,5-dihydro-1,2-oxazole-5-carbothioamide [ No CAS ]

Reference： [1]Patent: US2015/223461,2015,A1

22
[ 22620-34-4 ]
[ 113118-82-4 ]

Yield	Reaction Conditions	Operation in experiment
4.3 g	With sulfur trioxide pyridine complex; triethylamine; In dimethyl sulfoxide; at 50℃; for 3h;	(5-Chloropyridin-3-yl)methanol (6.3 g) was dissolved in dimethyl sulfoxide (12 ml), triethylamine (18.3 ml) was slowly added dropwise and the sulfur trioxide-pyridine complex (20.9 g) was added in portions (exothermicity: 50 C.). The reaction mixture was stirred for 3 h, adjusted to pH 3 with 2M hydrochloric acid and extracted by shaking twice with EtOAc. The organic phase was washed with saturated NaHCO3 solution, dried over MgSO4 and concentrated at 40 C. Yield: 4.3 g of 5-chloronicotinaldehyde.
128 mg	With manganese(IV) oxide; In dichloromethane; at 20℃;	To a solution of <strong>[22620-34-4](5-chloropyridin-3-yl)methanol</strong> (292 mg, 2.03 mmol) in dry DCM (10 ml) Mn02 (3.54 g, 40.6 mmol) was added. The mixture was stirred at rt o.n. The solid was filtered (washing with DCM) and the solution was evaporated to dryness to give the title compound (128 mg, 0.9 mmol, purity: 85 % by NIVIR, recovery: 44 %). MS (m/z) 142, 144(M+H).

Reference： [1]Patent: US2015/223461,2015,A1 .Location in patent: Paragraph 0255
[2]Patent: WO2016/185423,2016,A1 .Location in patent: Page/Page column 76

23
[ 402-43-7 ]
[ 113118-82-4 ]
(5-chloropyridin-3-yl)(4-(trifluoromethyl)phenyl)methanol [ No CAS ]