Home Cart 0 Sign in  

[ CAS No. 82671-02-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 82671-02-1
Chemical Structure| 82671-02-1
Structure of 82671-02-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 82671-02-1 ]

Related Doc. of [ 82671-02-1 ]

Alternatived Products of [ 82671-02-1 ]

Product Details of [ 82671-02-1 ]

CAS No. :82671-02-1 MDL No. :MFCD01863289
Formula : C6HCl2FN2 Boiling Point : -
Linear Structure Formula :- InChI Key :DEDKKOOGYIMMBC-UHFFFAOYSA-N
M.W : 190.99 Pubchem ID :2733849
Synonyms :

Calculated chemistry of [ 82671-02-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.93
TPSA : 36.68 Ų

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) : -5.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.58
Log Po/w (XLOGP3) : 2.59
Log Po/w (WLOGP) : 2.82
Log Po/w (MLOGP) : 1.43
Log Po/w (SILICOS-IT) : 3.05
Consensus Log Po/w : 2.29

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.06
Solubility : 0.167 mg/ml ; 0.000872 mol/l
Class : Soluble
Log S (Ali) : -3.01
Solubility : 0.187 mg/ml ; 0.000979 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.62
Solubility : 0.0453 mg/ml ; 0.000237 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.05

Safety of [ 82671-02-1 ]

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 [ 82671-02-1 ]

* 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 [ 82671-02-1 ]
  • Downstream synthetic route of [ 82671-02-1 ]

[ 82671-02-1 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 113237-18-6 ]
  • [ 82671-02-1 ]
Reference: [1] Patent: US5739342, 1998, A,
  • 2
  • [ 113237-18-6 ]
  • [ 107-06-2 ]
  • [ 82671-02-1 ]
Reference: [1] Patent: US5739342, 1998, A,
  • 3
  • [ 75993-41-8 ]
  • [ 82671-02-1 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 6, p. 2280 - 2285
  • 4
  • [ 82671-02-1 ]
  • [ 82671-06-5 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 12, p. 3211 - 3217
[2] Patent: US4649144, 1987, A,
[3] Patent: EP333020, 1991, A3,
  • 5
  • [ 100-70-9 ]
  • [ 82671-02-1 ]
  • [ 82671-06-5 ]
Reference: [1] Patent: US5739342, 1998, A,
  • 6
  • [ 82671-02-1 ]
  • [ 113237-20-0 ]
YieldReaction ConditionsOperation in experiment
99.5% at 62℃; for 1 h; Weigh 2,6-dichloro-5-fluoro-pyridine-3-carbonitrile (24.8 g, 130 mmol)Concentrated sulfuric acid (125 mL) was added to a 500 ml flask, and the mixture was heated to 62 ° C for 1 hour.After cooling to room temperature, the reaction solution was poured into ice water (800 mL) and ethyl acetate (300 mL×4).The organic phase was washed successively with water (100 mL), saturated sodium bicarbonate (100 mL) and brine (50 mL).Dry over anhydrous sodium sulfate.Filtered, the filtrate was dried,A pale yellow solid (27.0 g, 99.5percent).
91% at 60℃; for 2 h; A solution of 2,6-dichloro-5-fluoronicotinonitrile (60 g, 314 mmol) in concentrated H2SO4 (600 mL) was stirred for 2 h at 60 °C. After having cooled to 20°C, the reaction mixture was poured into ice-water, extracted with EtOAc (500 mL x 3), and the organic phase was dried over Na2S04 and concentrated under reduced pressure to give 2,6- dichloro-5-fluoronicotinamide (60 g, yield 91percent) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm: 8.24-8.22 (d, J = 8, 1H), 8.11 (s, 1H), 7.95 (s, 1H).
90%
Stage #1: at 60 - 65℃; for 1 h;
Stage #2: at 20℃; Cooling
Example 1A2,6-Dichloro-5-fluoronicotinamideA suspension of 25 g (130.90 mmol) of 2,6-dichloro-5-fluoro-3-cyanopyridine in cone, sulphuric acid (125 ml) was stirred at 60-65°C for 1 h. After cooling to RT, the contents of the flask were poured into ice-water and extracted three times with ethyl acetate (100 ml each time). The combined organic phases were washed with water (100 ml) and then with saturated aqueous sodium hydrogen carbonate solution (100 ml), dried and concentrated on a rotary evaporator. The material obtained was dried under a high vacuum.Yield: 24.5 g (90percent of theory).H NMR (400 MHz, DMSO-d6): δ = 7.95 (br s, 1H), 8.1 1 (br s, 1H), 8.24 (d, 1H).
90%
Stage #1: at 60 - 65℃; for 1 h;
Stage #2: With sodium hydrogencarbonate In water
Example 1A
2,6-Dichloro-5-fluoronicotinamide
A suspension of 25 g (130.90 mmol) of 2,6-dichloro-5-fluoro-3-cyanopyridine in conc. sulphuric acid (125 ml) was stirred at 60-65° C. for 1 h.
After cooling to RT, the contents of the flask were poured into ice-water and extracted three times with ethyl acetate (100 ml each time).
The combined organic phases were washed with water (100 ml) and then with saturated aqueous sodium hydrogen carbonate solution (100 ml), dried and concentrated on a rotary evaporator.
The material obtained was dried under high vacuum.
Yield: 24.5 g (90percent of theory)
1H NMR (400 MHz, DMSO-d6): δ=7.95 (br s, 1H), 8.11 (br s, 1H), 8.24 (d, 1H).
90% at 60 - 65℃; for 1 h; Example 2A
2,6-dichloro-5-fluoronicotinamide
A suspension of 25 g (130.90 mmol) of 2,6-dichloro-5-fluoro-3-cyanopyridine in conc. sulfuric acid (125 ml) was stirred at 60-65° C. for 1 h.
After cooling to RT, the contents of the flask were poured onto ice-water and extracted three times with ethyl acetate (100 ml each time).
The combined organic phases were washed with water (100 ml) and then with saturated aqueous sodium hydrogencarbonate solution (100 ml), dried and concentrated on a rotary evaporator.
The material obtained was dried under high vacuum.
Yield: 24.5 g (90percent of theory)
1H NMR (400 MHz, DMSO-d6): δ=7.95 (br s, 1H), 8.11 (br s, 1H), 8.24 (d, 1H).
90% at 60 - 65℃; for 1 h;
2,6-Dichloro-5-fluoronicotinamide
A suspension of 25 g (130.90 mmol) of 2,6-dichloro-5-fluoro-3-cyanopyridine in conc. sulfuric acid (125 ml) was stirred at 60-65° C. for 1 h.
After cooling to RT, the contents of the flask were poured into ice-water and extracted three times with ethyl acetate (100 ml each time).
The combined organic phases were washed with water (100 ml) and then with saturated aqueous sodium hydrogen carbonate solution (100 ml), dried and concentrated on a rotary evaporator.
The material obtained was dried under a high vacuum.
Yield: 24.5 g (90percent of theory)
1H-NMR (400 MHz, DMSO-d6): δ=7.95 (br s, 1H), 8.11 (br s, 1H), 8.24 (d, 1H).
90% at 60 - 65℃; for 1 h; Example 2A
2,6-Dichloro-5-fluoronicotinamide
A suspension of 25 g (130.90 mmol) of 2,6-dichloro-5-fluoro-3-cyanopyridine in conc. sulphuric acid (125 ml) was stirred for 1 h at 60-65° C.
After cooling to RT, the flask contents were poured into ice water and extracted with ethyl acetate three times (100 ml each time).
The combined organic phases were washed with water (100 ml) and then with saturated aqueous sodium hydrogen carbonate solution (100 ml), dried and concentrated in a rotary evaporator.
The material obtained was dried under high vacuum.
Yield: 24.5 g (90percent of theor.)
1H-NMR (400 MHz, DMSO-d6): δ=7.95 (br s, 1H), 8.11 (br s, 1H), 8.24 (d, 1H).
90% at 60 - 65℃; for 1 h; Example 19A
2,6-Dichloro-5-fluoronicotinamide
A suspension of 25 g (130.90 mmol) of 2,6-dichloro-5-fluoro-3-cyanopyridine in conc. sulfuric acid (125 ml) was stirred at 60-65° C. for 1 h.
After cooling to RT, the contents of the flask were poured onto ice-water and extracted three times with ethyl acetate (100 ml each time).
The combined organic phases were washed with water (100 ml) and then with saturated aqueous sodium hydrogencarbonate solution (100 ml), dried and concentrated on a rotary evaporator.
The material obtained was dried under high vacuum.
Yield: 24.5 g (90percent of theory)
1H NMR (400 MHz, DMSO-d6): δ=7.95 (br s, 1H), 8.11 (br s, 1H), 8.24 (d, 1H).
90% at 60 - 65℃; for 1 h; Example 1A
2,6-Dichloro-5-fluoronicotinamide
A suspension of 25 g (130.90 mmol) of 2,6-dichloro-5-fluoro-3-cyanopyridine in conc. sulphuric acid (125 ml) was stirred at 60-65° C. for 1 h.
After cooling to RT, the contents of the flask were poured into ice-water and extracted three times with ethyl acetate (100 ml each time).
The combined organic phases were washed with water (100 ml) and then with saturated aqueous sodium bicarbonate solution (100 ml), dried and concentrated on a rotary evaporator.
The material obtained was dried under a high vacuum.
Yield: 24.5 g (90percent of theory)
1H NMR (400 MHz, DMSO-d6): δ=7.95 (br s, 1H), 8.11 (br s, 1H), 8.24 (d, 1H).
90% at 60 - 65℃; for 1 h; A suspension of 25 g (130.90 mmol) of 2,6- dichloro-5-fluoro-3-cyanopyridine in conc. sulphuric acid (125 ml) was stirred at 60-65°C. for 1 h. Afier cooling to RT, the contents of the flask were poured into ice-water and extracted three times with ethyl acetate (100 ml each). The combined organic phases were washed with water (100 ml) and then washed with saturated aqueous sodium bicarbonate solution (100 ml), dried and concentrated on a rotary evaporator. The material obtained was dried under high vacuum.10410] Yield: 24.5 g (90percent of theory)10411] ‘H NMR (400 MHz, DMSO-d5): ö=7.95 (br s, 1H),
87%
Stage #1: at 65℃; for 1 h; Inert atmosphere; Large scale
Stage #2: at 0 - 20℃; for 1.58333 h; Inert atmosphere; Large scale
Step 1. 2,6-dichloro-5-fluoronicotinamide (2). [0293] 2,6-dichloro-5-fluoronicotinonitrile (1) was charged into a 50 L, jacketed, cylindrical reactor equipped with an overhead stirrer, thermocouple and N2 inlet and outlet. Concentrated sulfuric acid (27.22 kg, 4.93 vol) was added to the flask and agitation was started. The brown mixture was heated to 65 °C and stirred for 1 h and a clear brown solution was obtained. The dark brown mixture was then cooled to ambient temperature and then to <10 °C. While cooling, a separate 100 L, jacketed reactor was charged with deionized (DI) water (74.0 L, 24.7 vol) and the water was cooled to 0-5 °C. The reaction mixture was then transferred to the cooled water over one hour and thirty five minutes and the internal temperature was kept below 20 °C. The resulting slurry was filtered through an 18" Hastelloy Nutsche funnel with a polypropylene (PP) filter cloth. The 50 L reactor was rinsed with water (3 x 12 L, 3 x 4 vol) and the rinses were transferred to the funnel to wash the filter cake. The filter cake was conditioned for 16 hours and transferred to drying trays. The solid was dried under high vacuum at 40-50 °C for 29 h to give 2.856 kg of (2) as a beige solid in 87percent yield. 1 NMR (500 MHz, d6-DMSO) δ 8.23 (d, J = 7.9 Hz, 1H), 8.10 (s, 1H), 7.94 (s, 1H).
83% at 60℃; for 2 h; A stirred solution of 26-dichloro-5-fluoronicotinonitrile (100 g, 0.526 mol) in conc. H2S04(1000 mL) was heated at 60 °C for 2 h. After cooling to room temperature, the mixture waspoured into ice water, and extracted with EtOAc (300 mL x 3). The combined organic layerswere dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude residue,after being washed with hexane several times gave the title compound (90 g, 83percent yield) asa yellow solid. MS: 207.0 [M-Hr.
82% at 21 - 65℃; Inert atmosphere; Industry scale A. 2,6-Dichloro-5-fluoronicotinamide A 12-L 3-neck round bottom flask equipped with overhead stirrer, refluxing condenser, and N2 inlet/outlet was charged with 2,6-dichloro-5-fluoronicotinonitrile (2.0 kg, 1.0 eq). Concentrated sulfuric acid (4.93 L) was added and the mixture was stirred at RT until most of the brown solids had dissolved. Next, the reaction mixture was stirred at 65° C. for 1 h. The dark-brown solution was cooled to a temperature <10° C. using an ice bath. The reaction mixture was added to a 50-L round bottom flask, which contained de-ionized water (24.7 L) that had been cooled to a temperature <10° C., using a peristaltic pump. The reaction mixture was added to the water quench over a 2.3 h period, which kept the internal temperature of the mixture below 21° C. The resulting slurry was filtered through a Buchner funnel fitted with a Sharkskin filter paper. The 50-L RBF was rinsed with water (3.x.4 L) and the rinses were used to wash the filter cake. The filter cake was conditioned for 50 min, transferred to a drying tray, and was dried under high vacuum at 40-50° C. for 24 h and then at 20-25° C. for 18 h to give the title compound as a beige solid (896.4 g, 82percent). 1H NMR (500 MHz, DMSO-d6) δ ppm 7.94 (s, 1H), 8.10 (s, 1 H), 8.24 (d, 1H). [M+H] calc'd for C6H3Cl2FN2O, 209. found, 209.
24.5 g With sulfuric acid In sulfuric acid at 60 - 65℃; for 1 h; A suspension of 25 g (130.90 mmol) of 2,6-dichloro-5-fluoro-3-cyanopyridine in conc. sulphuric acid (125 ml) was stirred at 60-65° C. for 1 h.
After cooling to RT, the contents of the flask were poured onto ice-water and extracted three times with ethyl acetate (100 ml each time).
The combined organic phases were washed with water (100 ml) and then with saturated aqueous sodium bicarbonate solution (100 ml), dried and concentrated on a rotary evaporator.
The material obtained was dried under high vacuum.
Yield: 24.5 g (90percent of theory)
1H NMR (400 MHz, DMSO-d6): δ=7.95 (br s, 1H), 8.11 (br s, 1H), 8.24 (d, 1H).

Reference: [1] Patent: CN108690016, 2018, A, . Location in patent: Paragraph 0366; 0368; 0369
[2] Patent: WO2017/50807, 2017, A1, . Location in patent: Page/Page column 132
[3] Patent: WO2011/147810, 2011, A1, . Location in patent: Page/Page column 24
[4] Patent: US2012/22084, 2012, A1, . Location in patent: Page/Page column 14
[5] Patent: US2013/172372, 2013, A1, . Location in patent: Paragraph 0238; 0239; 0240; 0241
[6] Patent: US2013/158028, 2013, A1, . Location in patent: Paragraph 0106-0109
[7] Patent: US2013/338137, 2013, A1, . Location in patent: Paragraph 1436; 1437; 1438; 1439
[8] Patent: US2014/148433, 2014, A1, . Location in patent: Paragraph 0670; 0671; 0672
[9] Patent: US2014/228366, 2014, A1, . Location in patent: Paragraph 0576; 0577; 0578; 0579
[10] Patent: US2014/350020, 2014, A1, . Location in patent: Paragraph 0408; 0409; 0410; 0411; 0324
[11] Patent: WO2016/97862, 2016, A2, . Location in patent: Paragraph 0292-0293
[12] Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 6, p. 2280 - 2285
[13] Patent: WO2017/133664, 2017, A1, . Location in patent: Page/Page column 62; 63
[14] Patent: WO2017/133667, 2017, A1, . Location in patent: Page/Page column 103
[15] Patent: US2011/152273, 2011, A1, . Location in patent: Page/Page column 99
[16] Patent: US2014/100229, 2014, A1, . Location in patent: Page/Page column
[17] Patent: US2014/357637, 2014, A1, . Location in patent: Paragraph 0985 - 0988
  • 7
  • [ 100-70-9 ]
  • [ 82671-02-1 ]
  • [ 107-06-2 ]
  • [ 113237-20-0 ]
Reference: [1] Patent: US5739342, 1998, A,
  • 8
  • [ 82671-02-1 ]
  • [ 870065-73-9 ]
YieldReaction ConditionsOperation in experiment
76% With potassium fluoride In dimethyl sulfoxide at 20 - 130℃; for 0.916667 h; 2,6-Dichloro-5-fluoro-nicotinonitrile (25.67 g, 134 mmol) and spray-dried KF (23.6 g, 406 mmol) (Aldrich), both of which had been freshly powdered under air to remove clumps, were shaken together to ensure complete mixing before adding dry DMSO (30 mL). The mixture was efficiently stirred at rt under argon for 1-2 min, and then placed in a 100° C. oil bath and stirred for 5 min. The temperature was then raised to 130° C. over the course of 10 min, and the mixture was stirred at this temperature for 40 min. The NMR spectrum of reaction aliquots demonstrated 86percent conversion after 10 min at 130° C., and >95percent conversion after 40 min. The thick purple mixture was then allowed to cool to rt, shaken with DCM (30 mL) on an ice bath, and then loaded directly onto a flash silica column (1.0 kg silica gel; 120 mm.x.6) pre-equilibrated with DCM. DCM elution (140 mL fractions; fractions 10-19 combined) afforded 20.65 g of a clear light amber oil. A NMR spectrum demonstrated a 1:0.58 mol ratio of title compound:DMSO (16.0 g title compound; 76percent). 1H-NMR (300 MHz, CDCl3) δ 7.99 (m, 1H). LC/MS (ESI): calcd mass 158.0, found 159.5 (MH)+
Reference: [1] Patent: US2006/241148, 2006, A1, . Location in patent: Page/Page column 12
  • 9
  • [ 82671-02-1 ]
  • [ 791644-48-9 ]
Reference: [1] Patent: WO2011/147810, 2011, A1,
[2] Patent: US2012/22084, 2012, A1,
[3] Patent: US2013/172372, 2013, A1,
[4] Patent: US2013/158028, 2013, A1,
[5] Patent: US2013/338137, 2013, A1,
[6] Patent: US2014/100229, 2014, A1,
[7] Patent: US2014/148433, 2014, A1,
[8] Patent: US2014/228366, 2014, A1,
[9] Patent: US2014/357637, 2014, A1,
[10] Patent: US2014/350020, 2014, A1,
[11] Patent: WO2017/133664, 2017, A1,
[12] Patent: WO2017/133667, 2017, A1,
[13] Patent: CN108690016, 2018, A,
  • 10
  • [ 82671-02-1 ]
  • [ 1034667-22-5 ]
Reference: [1] Patent: WO2011/147810, 2011, A1,
[2] Patent: US2012/22084, 2012, A1,
[3] Patent: US2013/172372, 2013, A1,
[4] Patent: US2013/158028, 2013, A1,
[5] Patent: US2013/338137, 2013, A1,
[6] Patent: US2014/100229, 2014, A1,
[7] Patent: US2014/148433, 2014, A1,
[8] Patent: US2014/228366, 2014, A1,
[9] Patent: US2014/357637, 2014, A1,
[10] Patent: US2014/350020, 2014, A1,
[11] Patent: WO2017/133664, 2017, A1,
[12] Patent: WO2017/133667, 2017, A1,
[13] Patent: CN108690016, 2018, A,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 82671-02-1 ]

Fluorinated Building Blocks

Chemical Structure| 1020253-14-8

[ 1020253-14-8 ]

6-Chloro-5-fluoronicotinonitrile

Similarity: 0.84

Chemical Structure| 52208-50-1

[ 52208-50-1 ]

2,6-Dichloro-3-fluoropyridine

Similarity: 0.78

Chemical Structure| 34552-15-3

[ 34552-15-3 ]

2-Chloro-3-fluoro-5-methylpyridine

Similarity: 0.74

Chemical Structure| 113237-20-0

[ 113237-20-0 ]

2,6-Dichloro-5-fluoronicotinamide

Similarity: 0.73

Chemical Structure| 13600-42-5

[ 13600-42-5 ]

2,6-Dichloro-4-(trifluoromethyl)nicotinonitrile

Similarity: 0.70

Chlorides

Chemical Structure| 1020253-14-8

[ 1020253-14-8 ]

6-Chloro-5-fluoronicotinonitrile

Similarity: 0.84

Chemical Structure| 52208-50-1

[ 52208-50-1 ]

2,6-Dichloro-3-fluoropyridine

Similarity: 0.78

Chemical Structure| 875-35-4

[ 875-35-4 ]

2,6-Dichloro-4-methylnicotinonitrile

Similarity: 0.78

Chemical Structure| 40381-92-8

[ 40381-92-8 ]

2,5,6-Trichloronicotinonitrile

Similarity: 0.74

Chemical Structure| 34552-15-3

[ 34552-15-3 ]

2-Chloro-3-fluoro-5-methylpyridine

Similarity: 0.74

Nitriles

Chemical Structure| 1020253-14-8

[ 1020253-14-8 ]

6-Chloro-5-fluoronicotinonitrile

Similarity: 0.84

Chemical Structure| 875-35-4

[ 875-35-4 ]

2,6-Dichloro-4-methylnicotinonitrile

Similarity: 0.78

Chemical Structure| 40381-92-8

[ 40381-92-8 ]

2,5,6-Trichloronicotinonitrile

Similarity: 0.74

Chemical Structure| 32710-65-9

[ 32710-65-9 ]

2,6-Dichloroisonicotinonitrile

Similarity: 0.74

Chemical Structure| 10177-06-7

[ 10177-06-7 ]

2,6-Dichloro-5-phenylnicotinonitrile

Similarity: 0.71

Related Parent Nucleus of
[ 82671-02-1 ]

Pyridines

Chemical Structure| 1020253-14-8

[ 1020253-14-8 ]

6-Chloro-5-fluoronicotinonitrile

Similarity: 0.84

Chemical Structure| 52208-50-1

[ 52208-50-1 ]

2,6-Dichloro-3-fluoropyridine

Similarity: 0.78

Chemical Structure| 875-35-4

[ 875-35-4 ]

2,6-Dichloro-4-methylnicotinonitrile

Similarity: 0.78

Chemical Structure| 40381-92-8

[ 40381-92-8 ]

2,5,6-Trichloronicotinonitrile

Similarity: 0.74

Chemical Structure| 34552-15-3

[ 34552-15-3 ]

2-Chloro-3-fluoro-5-methylpyridine

Similarity: 0.74