[ CAS No. 16179-97-8 ] {[proInfo.proName]}

Name: 16179-97-8|2-(Pyridin-2-yl)acetic acid hydrochloride|95%
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SKU: A263007
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Quality Control of [ 16179-97-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 16179-97-8 ]

SDS Specification

Alternatived Products of [ 16179-97-8 ]

Product Details of [ 16179-97-8 ]

CAS No. :	16179-97-8	MDL No. :	MFCD00012812
Formula :	C₇H₈ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MQVISALTZUNQSK-UHFFFAOYSA-N
M.W :	173.60	Pubchem ID :	85317
Synonyms :	2-(Pyridin-2-yl)acetic acid hydrochloride

Calculated chemistry of [ 16179-97-8 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	42.75
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) :	-6.79 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.8
Log Po/w (WLOGP) :	1.51
Log Po/w (MLOGP) :	0.39
Log Po/w (SILICOS-IT) :	1.04
Consensus Log Po/w :	0.75

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 :	3.53 mg/ml ; 0.0203 mol/l
Class :	Very soluble
Log S (Ali) :	-1.44
Solubility :	6.37 mg/ml ; 0.0367 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.77
Solubility :	2.93 mg/ml ; 0.0169 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.47

Safety of [ 16179-97-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 16179-97-8 ]

* 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 [ 16179-97-8 ]
Downstream synthetic route of [ 16179-97-8 ]

[ 16179-97-8 ] Synthesis Path-Upstream 1~4

1
[ 67-56-1 ]
[ 16179-97-8 ]
[ 1658-42-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: at 0 - 20℃; Inert atmosphere Stage #2: With sodium hydrogencarbonate In water	S2 was prepared analogously to a published procedure.13 2.00 g S1 (11.5 mmol, 1.00 equiv.) and 14 mL MeOH were added to a round-bottom flask. The solution was cooled to 0 °C, and 2.90 mL TMSCl (23.0 mmol, 2.00 equiv.) were added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. The solvent was then removed in vacuo, ant the remaining solid was treated slowly with sat. aq. NaHCO3 (40 mL). The aqueous solution was extracted with CH2Cl2 (4 x 40 mL), and the combined organic extracts were dried over Na2SO4, filtered, and the solvent was removed in vacuo. The crude product (S2) was isolated as a clear oil (1.73 g, 11.47 mmol, quant.). The spectral data of the compound were compared with the published ones.13
95%	at 0℃; for 1 h;	To a solution of 2-(pyridin-2-yl)acetic acid hydrochloride salt MMMMMM (50.0 g, 288.0 mmol, 1.0 equiv.) in methanol (500 mL, 0.5M) at 0 °C was added thionyl chloride (31.5 mL, 432.0 mmol, 1.5 equiv.) dropwise. The reaction was stirred at 0 °C for 60 minutes or until the reaction was determined to be complete by LCMS or TLC. The reaction was carefully quenched with sodium carbonate and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting product (NNNNNN, 41.5 g, 275.0 mmol, 95percent) was used in the next step without further purification.

Reference： [1] Tetrahedron, 2011, vol. 67, # 24, p. 4435 - 4441
[2] Patent: WO2017/87667, 2017, A1, . Location in patent: Paragraph 0069
[3] Journal of the American Chemical Society, 2015, vol. 137, # 32, p. 10246 - 10253
[4] Journal of Organic Chemistry, 2001, vol. 66, # 20, p. 6595 - 6603

2
[ 16179-97-8 ]
[ 1658-42-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With thionyl chloride In methanol at 0℃; for 1 h;	Step 1: To a solution of 2-(pyridin-2-yl)acetic acid hydrochloride salt MMMMMM (50.0 g, 288.0 mmol, 1.0 equiv.) in methanol (500 mL, 0.5M) at 0° C. was added thionyl chloride (31.5 mL, 432.0 mmol, 1.5 equiv.) dropwise. The reaction was stirred at 0° C. for 60 minutes or until the reaction was determined to be complete by LCMS or TLC. The reaction was carefully quenched with sodium carbonate and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting product (NNNNNN, 41.5 g, 275.0 mmol, 95percent) was used in the next step without further purification.

Reference： [1] Patent: US2015/329528, 2015, A1, . Location in patent: Paragraph 0099; 0100

3
[ 186581-53-3 ]
[ 16179-97-8 ]
[ 1658-42-0 ]

Reference： [1] Journal of the American Chemical Society, 2004, vol. 126, # 48, p. 15777 - 15783

4
[ 1439399-45-7 ]
[ 16179-97-8 ]
[ 1439399-58-2 ]

Reference： [1] Patent: WO2013/78123, 2013, A1, . Location in patent: Page/Page column 152; 153

[ 16179-97-8 ] Synthesis Path-Downstream 1~18

1
(2R*,4S*)-2-benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine [ No CAS ]
[ 68641-49-6 ]
[ 16179-97-8 ]
(2R*,4S*)-2-benzyl-1-(pyridin-2-ylacetyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;	(2R,4S)-2-Benzyl-1-(2-pyridylacetyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine 200 mg (0.467 mmol) of (2R,4S)-2-benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine are reacted in analogy to Example 4 with 98 mg (0.561 mmol) of 2-pyridylacetic acid hydrochloride, 143 mg (0.562 mmol) of bis-(2-oxo-3-oxazolidinyl)phosphinic chloride and 209 mul (1.50 mmol) of triethylamine. The title compound is obtained as white foam. TLC: methylene chloride/methanol/conc. ammonia (700:50:1) Rf =0.60, FD-MS: M+ =546.

Reference： [1]Patent: US5310743,1994,A

2
[ 5900-58-3 ]
[ 13115-43-0 ]
[ 68641-49-6 ]
[ 16179-97-8 ]
[ 139422-30-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In 1,2-dichloro-ethane;	EXAMPLE 62 7-Chloro-2,4-dioxo-3-(2-pyridyl)-1,2,3,4-tetrahydroquinoline To a solution of methyl 2-amino-4-chlorobenzoate (2 g, 10.8 mmol) in 1,2-dichlorethane (60 ml) was added 2-pyridylacetic acid hydrochloride (1.9 g, 10.8 mmol), triethylamine (3.2 ml, 22.7 mmol) and bis (2-oxo-3-oxazolidinyl)phosphinic chloride and the reaction refluxed for 8 h. More 2-pyridylacetic acid (1.9 g, 10.8 mmol) and triethylamine (3.2 ml, 22.7 mmol) were added and refluxing continued for a further 16 h. The solvent was evaporated and the residue partitioned between saturated aqueous sodium bicarbonate solution (50 ml) and dichloromethane (50 ml). The organic phase was dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica (eluding with 50% ethyl acetate/60-90 petrol) to afford methyl 4-chloro-2-(3-pyridyl)acetamidobenzoate as a green solid (2.5 g), m.p. 85-87 C.

Reference： [1]Patent: US5268378,1993,A

3
[ 22190-33-6 ]
[ 16179-97-8 ]
5-bromo-1-(2-pyridinylacetyl)indoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 20h;	31 Preparation 31 EPO To a solution of 5-bromoindoline (5.Og) , 2-pyridinylacetic acid hydrochloride (4.82 g) and benzotriazol-1-yl- oxytripyrrolidinophosphoniumhexafluorophosphate (PyBOP) (15.8 g) in N, N-dimethylformamide (100 mL) was added dropwise diisoprpylethylamine (6.53 g) at ambient temperature and the mixture was stirred at the same temperature for 20 hours. The mixture was poured into a mixture of ethyl acetate and water and the separated organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to give 5-bromo-l- (2-pyridinylacetyl) indoline (5.23 g) as a light-brown powder.IH-NMR (DMSO-dβ) : 53.16 (2H, t, J=6.8 Hz), 4.01(2H, s), 4.22(2H, t, J=6.8 Hz) , 7.25-7.45 (4H, m) , 7.7-7.8 (IH, m) , 7.98 (IH, d, J=8.7 Hz) , 8.45-8.5 (IH, m)ESI-MS (m/z): 319,317 (M+Na)

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - WO2007/26920, 2007, A2 Location in patent: Page/Page column 29-30

4
[ 5466-88-6 ]
[ 16179-97-8 ]
6-(pyridin-2-ylacetyl)-2H-1,4-benzoxazin-3(4H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3,4-dihydro-3-oxo-2H-1,4-benzoxazine; pyridin-2-yl acetic acid hydrochloride With PPA at 80 - 130℃; for 24.5h; Stage #2: With sodium hydroxide In water at 60℃; for 2h;	30 To a mixture of 2H-1, 4-benzoxazin-3 (4H) -one (5.0 g) and polyphosphoric acid (150 g) was added 2-pyridylacetic acid hydrochloride (8.7 g) at 800C and the mixture was stirred for 0.5 hr. The mixture was allowed to warm to 1300C and stirred for 24 hr. The mixture was added to ice-cooled water (300 ml) . The aqueous mixture was filtered and the filtrate was adjusted to pH 8 by the addition of 8N-NaOH. The mixture was stirred at 600C for 2 hr and then cooled to 500C. The resulting crystals were collected by filtration and washed with water. The crystals were suspended in methanol and the mixture was refluxed for 1 hr. After cooling the mixture to room temperature, the resulting crystals were collected. The title compound was obtained as crystals (4.0 g) . Anal. Calcd for C15H12N2O3: C, 67.16; H, 4.51; N, 10.44. Found: 67.87; H, 4.46; N, 10.39.

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2007/77961, 2007, A2 Location in patent: Page/Page column 248

5
[ 14667-47-1 ]
[ 16179-97-8 ]
[ 1173016-80-2 ]

Yield	Reaction Conditions	Operation in experiment
		Example 1.3: Preparation of 2-(2-pyridin-2-yl-acetylamino')-nicotinic acid methyl ester; To a solution of 2-pyridyl-acetic acid hydrochloride (310 mg) and 2-amino- nicotinic acid methyl ester (270 mg) (Example 1.1) in dichloromethane (5ml) was added diisopropylethylamine (0.32 ml). The reaction mixture was stirred at ambient temperature for 20 minutes. To this solution was added 4-dimethylaminopyridine (43 mg) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride ("EDAC") (410 mg). The reaction mixture was stirred at ambient temperature for 20 hours. The reaction mixture was partitioned between dichloromethane and water. The phases were separated and the the organic layer concentrated. The residue was purified by column chromatography on silica gel (eluent: 15% acetone in dichloromethane) to give 2-(2- pyridin-2-yl-acetylamino)-nicotinic acid methyl ester as a yellow solid (86 mg). IH- NMR (400 MHz, CDCl3): 11.14 (bs, IH), 8.63-8.64 (m, IH), 8.58-8.59 (dd, IH), 8.25- <n="50"/>8.27 (dd, IH), 7.66-7.70 (m, IH), 7.38 (d, IH)," 7.20-7.23 (m, IH), 7.05-7.08 (dd, IH), 4.11 (s, 2H), 3.92 (s, 3H) ppm.

Reference： [1]Patent: WO2009/90401,2009,A2 .Location in patent: Page/Page column 48-49

6
[ 16179-97-8 ]
[ 19615-30-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen;platinum(IV) oxide; In methanol; for 2.0h;	Synthesis of 2-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-2-yl)acetic acid (AC2)Stage 1. 2-(Piperidinyl-2-yl)acetic acid hydrochloridePtθ2 (0.8 g, moistened with methanol) was added to a solution of 2-(pyridin-2-yl)acetic acid hydrochloride (20 g) in methanol (200 ml) and the mixture was stirred under a hydrogen atmosphere for 2 hours. The reaction was monitored by means of thin layer chromatography and the mixture was filtered over Celite when the conversion was complete. The filtrate was concentrated in vacuo. The yield was 20.5 g (quantitative).

Reference： [1]Patent: WO2009/124746,2009,A1 .Location in patent: Page/Page column 92

7
[ 159184-15-3 ]
[ 16179-97-8 ]
tert-butyl N-[2-(4-[2-(2-pyridyl)acetyl]amino}phenoxy)ethyl]carbamate [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2010,vol. 58,p. 533 - 545

8
[ 2795-41-7 ]
[ 16179-97-8 ]
[ 1316695-11-0 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 5320 - 5334

9
[ 1439399-45-7 ]
[ 16179-97-8 ]
[ 1439399-58-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 1.0h;	General procedure: A flask was charged with 657 (50 mg, 0.111 mmol), 2-pyridine acetic acid hydrochloride (20 mg, 0.116 mmol) in DMF (1 ml) at 0 C was treated with propylphosphonic anhydride solution (91 ul) followed by triethylamine (40 ul, 0.29 mmol). The resulting mixture was slowly warmed up to room temperature and stirred for 1 h before it was quenched by addition of ice water (~5 mL). The yellow precipitate was collected by suction filtration, rinsed with more water. The crude material was purified by silica gel chromatography eluting with 0-6% MeOH in dichloromethane to afford 670. 1H NMR (300 MHz, DMSO-d6) delta 12.67 (s, 1H), 11.32 (s, 1H), 8.53-8.49 (m, 1H), 8.22-8.19 (d, J= 9.12 Hz, 1H), 7.78-7.76 (t, 1H), 7.58-7.26 (m, 7H), 4.01 (s, 2H), 3.87 (s, 2H), 3.01 (bs, 2H), 2.90 (bs, 2H), 1.73 (bs, 4H).

Reference： [1]Patent: WO2013/78123,2013,A1 .Location in patent: Page/Page column 152; 153

10
[ 1477-68-5 ]
[ 16179-97-8 ]
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-(pyridin-2-yl)acetamide [ No CAS ]

Reference： [1]ACS Chemical Neuroscience,2018,vol. 9,p. 587 - 602

11
[ 531-81-7 ]
[ 16179-97-8 ]
[ 1542158-09-7 ]