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[ CAS No. 61494-55-1 ] {[proInfo.proName]}

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Chemical Structure| 61494-55-1
Chemical Structure| 61494-55-1
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Product Details of [ 61494-55-1 ]

CAS No. :61494-55-1 MDL No. :MFCD09757512
Formula : C7H6ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :NOASBJYTBZMVKT-UHFFFAOYSA-N
M.W : 171.58 Pubchem ID :14739544
Synonyms :

Calculated chemistry of [ 61494-55-1 ]      Expand+

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 : 40.79
TPSA : 50.19 Ų

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) : -6.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.16
Log Po/w (XLOGP3) : 1.28
Log Po/w (WLOGP) : 1.36
Log Po/w (MLOGP) : 0.66
Log Po/w (SILICOS-IT) : 1.69
Consensus Log Po/w : 1.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.98
Solubility : 1.79 mg/ml ; 0.0104 mol/l
Class : Very soluble
Log S (Ali) : -1.93
Solubility : 2.0 mg/ml ; 0.0117 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.41
Solubility : 0.661 mg/ml ; 0.00385 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.59

Safety of [ 61494-55-1 ]

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 [ 61494-55-1 ]

* 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 [ 61494-55-1 ]
  • Downstream synthetic route of [ 61494-55-1 ]

[ 61494-55-1 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 101012-32-2 ]
  • [ 61494-55-1 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: for 0.583333 h; Reflux
Stage #2: With hydrogenchloride In water at 0℃; for 1 h;
A solution of 15percent w/w NaOH (15 mL) was added to (2-chloropyridin-3-yl)acetonitrile (1116) (0.932 g, 6.1 mmol). The mixture was heated at reflux for 35 minutes then cooled to room temperature. The mixture was further cooled to 0 °C and then acidified with cone. HCI (ca 5 mL) to pH 1. The suspension was left to stand for 1 hour in an ice bath. The precipitate was filtered and washed with cold propan-2-ol (3x15 mL) to yield the title compound (1117) (1 .05 g, 100percent) as an off-white solid; 1H NMR (400 MHz, d6-DMSO) δ 12.63 (s, 1 H), 8.32 (dd, J = 4.8, 1.9 Hz, 1 H), 7.86 (dd, J = 7.5, 1.9 Hz, 1 H), 7.41 (dd, J = 7.5, 4.8 Hz, 1 H), 3.75 (s, 2H). LCMS Method C: rt 4.06 min; m/z 172 [M+Hf.
100% for 0.583333 h; Reflux A solution of 15percent w/w NaOH (15 mL) was added to (2-chioropyridin-3-yl)acetonitrile (1116) (0.932 g, 6.11 mmol). The mixture was heated at reflux for 35 minutes then cooled to room temperature. The mixture was further cooled to 0 °C and then acidified with cone. HCi (ca 5 mL) to pH 1. The suspension was left to stand for 1 hour in an ice bath. The precipitate was filtered and washed with cold propan-2~ol (3x15 mL) to yield the title compound (1117) (1.05 g, 100percent) as an off-white solid; 1H NMR (400 MHz, cfe-DMSO) δ 12.63 (s, 1 H), 8.32 (dd, J = 4.8, 1.9 Hz, 1 H), 7.86 (dd, J = 7.5, 1.9 Hz, 1 H), 7.41 (dd, J = 7.5, 4.8 Hz, 1 H), 3.75 (s, 2H). LCMS Method C: rt 4.06 min; m/z 172 [M+H]+.
90%
Stage #1: With sodium hydroxide In water for 0.5 h; Heating / reflux
Stage #2: With hydrogenchloride In water at 0 - 10℃;
(2-Chloropyridin-3-yl)acetic acidTo a 2 L reactor, set for reflux, was stirred a pre-prepared 15percent w/w solution of sodium hydroxide (5 vols) to which was added (2-chloropyridin-3-yl)acetonitrile (Intermediate 2\\ 276.4 g, 1.81M). The beige suspension was heated to reflux for 30 minutes, at which point the reaction was deemed complete by HPLC. The brown solution was then cooled to 0-50C and acidified to pH 1 with cone. HCl while keeping the temperature below 1O C, using concentrated hydrochloric acid (1.8 vols). An off-white solid precipitated and was left to mature for another hour before filtration. Once dried, the material was recrystallised from propan-2-ol (4 vols) to afford the title compound as an off-white material in excellent yield and purity (280.3 g, 90percent). ?H (d?-DMSO, 300 MHz) 12.70 (IH, s), 8.35 (IH, dd), 7.85 (IH, dd), 7.40 (IH, dd), 4.25 (2H, s). LCMS (ES)+ RT 1.75 min, m/e 171.99 (M+l, Product).
90%
Stage #1: With sodium hydroxide In water for 0.5 h; Reflux
Stage #2: With hydrogenchloride In water at 0 - 10℃;
(2-Chloropyridin-3-yl)acetic acid To a 2 L reactor, set for reflux, was stirred a pre-prepared 15percent w/w solution of sodium hydroxide (5 vols) to which was added (2-chloropyridin-3-yl)acetonitrile (Intermediate 2; 276.4 g, 1.81M). The beige suspension was heated to reflux for 30 minutes, at which point the reaction was deemed complete by HPLC. The brown solution was then cooled to 0-50C and acidified to pH 1 with cone. HCl while keeping the temperature below 1O0C, using concentrated hydrochloric acid (1.8 vols). An off-white solid precipitated and was left to mature for another hour before filtration. Once dried, the material was recrystallised from propan-2-ol (4 vols) to afford the title compound as an off-white material in excellent yield and purity (280.3 g, 90percent). δH (d6-DMSO, 300 <n="27"/>MHz) 12.70 (IH, s), 8.35 (IH, dd), 7.85 (IH, dd), 7.40 (IH, dd), 4.25 (2H, s). LCMS (ES)+ RT 1.75 min, m/e 171.99 (M+l, Product).
90%
Stage #1: for 0.5 h; Reflux
Stage #2: With hydrogenchloride In water at 0 - 10℃;
INTERMEDIATE 3(2-Chloropyridin-3-yl)acetic acidTo a 2 L reactor, set for reflux, was stirred a pre-prepared 15percent w/w solution of sodium hydroxide (5 vols) to which was added (2-chloropyridin-3-yl)acetonitrile {Intermediate 2; 216 A g, 1.81M). The beige suspension was heated to reflux for 30 minutes, at which point the reaction was deemed complete by HPLC. The brown solution was then cooled to 0-50C and acidified to pH 1 with cone. HCl while keeping the temperature below 1O0C, using concentrated hydrochloric acid (1.8 vols). An off-white solid precipitated and was left to mature for another hour before filtration. Once dried, the material was recrystallised from propan-2-ol (4 vols) to afford the title compound as an off-white material in excellent yield and purity (280.3 g, 90percent). δH (d6-DMSO, 300 MHz) 12.70 (IH, s), 8.35 (IH, dd), 7.85 (IH, dd), 7.40 (IH, dd), 4.25 (2H, s). LCMS (ES)+ RT 1.75 min, m/e 171.99 (M+l, Product).
80% at 0 - 90℃; for 4 h; (Step 4)
To a solution of the compound (11.7 g) obtained in step 3 in water (66 mL) was added concentrated sulfuric acid (55.6 mL) at 0°C, and the mixture was stirred at 90°C for 4 hr.
The reaction mixture was poured into ice-cold water, and the precipitate was filtered off.
The filtrate was extracted three times with ethyl acetate.
The organic layer was washed with brine, and concentrated to give (2-chloropyridin-3-yl)acetic acid (10.5 g, 80percent) as a white powder.
1H-NMR(CDCl3+DMSO-d6): δ 3.75(2H,s), 7.25(1H,dd,J=7.4,4.8Hz), 7.69(1H,dd,J=7.4,1.8Hz), 8.31(1H,dd,J=4.8,1.8Hz)
39% at 100℃; for 2 h; (2-Chloropyridin-3-yl)acetonitrile (1.0 g, 6.55 mmol) in conc. hydrochloric acid (15 mL) is stirred at 100° C. for 2 hr. After cooling to room temperature the reaction mixture is diluted with water and the solution is concentrated to dryness. The residue is dissolved in water, made basic with ammonium hydroxide, re-acidified with acetic acid and extracted with ethyl acetate. The combined extract is washed with brine, dried, filtered and concentrated to give (2-chloropyridin-3-yl)acetic acid (442 mg, 39percent) as a white solid.

Reference: [1] Patent: WO2012/110773, 2012, A1, . Location in patent: Page/Page column 138; 139
[2] Patent: WO2014/27199, 2014, A1, . Location in patent: Page/Page column 141
[3] Patent: WO2009/13462, 2009, A1, . Location in patent: Page/Page column 26
[4] Patent: WO2009/93008, 2009, A1, . Location in patent: Page/Page column 25-26
[5] Patent: WO2009/153554, 2009, A1, . Location in patent: Page/Page column 36
[6] Patent: EP2018863, 2009, A1, . Location in patent: Page/Page column 74
[7] Patent: US2005/54631, 2005, A1, . Location in patent: Page/Page column 24
[8] Journal of the American Chemical Society, 1959, vol. 81, p. 740,742
[9] Journal of Medicinal Chemistry, 1990, vol. 33, # 10, p. 2697 - 2706
[10] Patent: WO2007/88345, 2007, A1, . Location in patent: Page/Page column 23
  • 2
  • [ 773837-37-9 ]
  • [ 89581-84-0 ]
  • [ 61494-55-1 ]
YieldReaction ConditionsOperation in experiment
92.1% With hydroquinone In ethanol; water at 60 - 70℃; NaCN (1.3 mol) was dissolved in water (100 g) and 202 g of ethanol and 1 g of the polymerization inhibitor hydroquinone were added,When the temperature was raised to 60 ° C, 2-chloro-3-chloromethylpyridine (total amount 1 mol) was added in batches, and the mixture was heated to 70The reaction was carried out for 2-3 hours (central control). After completion of the reaction, the reaction mixture was dehydrated and eluted with water, and water (330 g) was added dropwise with NaOH (1.3 mol)(30percent), dropping at 50 for 15min, after the drop in the temperature of the reaction at this temperature 30min, after the temperature to 80 to the anti-Should be completed (in control), micro-negative pressure deamination, ammonia after completion (removal of ammonia is about 150g), cooling, plus activated carbon release polymer(Decolorization), filtration, the filtrate dropwise hydrochloric acid acid (pH 3-4), cooling and filtration,The solid 2-chloro-3-pyridineacetic acid (CAS: 61494-55-1) was washed with water,Vacuum drying 157.8 g,The quantitative content of HPLC was 99.5percent and the yield was 92.1percent.
Reference: [1] Patent: CN106366034, 2017, A, . Location in patent: Paragraph 0021; 0022; 0026; 0027
  • 3
  • [ 6443-85-2 ]
  • [ 61494-55-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 10, p. 2697 - 2706
[2] Journal of the American Chemical Society, 1959, vol. 81, p. 740,742
[3] Patent: WO2012/110773, 2012, A1,
[4] Patent: WO2014/27199, 2014, A1,
  • 4
  • [ 6635-88-7 ]
  • [ 61494-55-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 10, p. 2697 - 2706
[2] Journal of the American Chemical Society, 1959, vol. 81, p. 740,742
[3] Patent: WO2012/110773, 2012, A1,
[4] Patent: WO2014/27199, 2014, A1,
  • 5
  • [ 6959-48-4 ]
  • [ 61494-55-1 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 740,742
  • 6
  • [ 89581-84-0 ]
  • [ 61494-55-1 ]
Reference: [1] Patent: WO2009/153554, 2009, A1,
  • 7
  • [ 42330-59-6 ]
  • [ 61494-55-1 ]
Reference: [1] Patent: WO2009/153554, 2009, A1,
  • 8
  • [ 61494-55-1 ]
  • [ 6419-36-9 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With sodium hydroxide In water at 50 - 95℃;
Stage #2: With hydrogen In water at 90 - 95℃;
Stage #3: With hydrogenchloride In water
2-chloro-3-pyridineacetic acid 50 g,Prepared into a 25percent mass fraction of 2-chloro-3-pyridine sodium acetate solution,And 47 g of a 30percent sodium hydroxide solutionSouring (the system may produce some insoluble polymer),Stir evenly after filtration,In the filtrate, 20percent of Raney nickel catalyst was added,Heating up to 90-95 ,Through hydrogen reaction,In the atmospheric pressure or 1MPa pressure environment reaction,In the control,After the reaction is completed,After filtering the catalyst,The filtrate was adjusted to pH 4 with hydrochloric acid,Activated charcoal decolorization, desolate, offDry solvent (into a viscous fluid,And there is crystal presence (NaCl)Add 100 grams of anhydrous ethanol, fully dissolved,Filtration, the filtrate is 3-pyridine acetic acid in ethanol solution,The ethanol in the solution was removed (dried,Into a viscous fluid, can be added to the back of the amount of water,Dry the ethanol)Add water 50g, and add hydrochloric acid 35g,After sufficiently salt formation at 50 ° C,The solvent water is then dried (viscous solid)Cooling to room temperature,Plus 50g of absolute ethanol after washing,After filtration, the solid was rinsed with a portion of ethanol,Dry, that was finished3-pyridine acetic acid hydrochloride47.5 g, purity 99.1percent, yield 95.0percent.
Reference: [1] Patent: CN106366034, 2017, A, . Location in patent: Paragraph 0020; 0023; 0024; 0025; 0028; 0029
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