[ CAS No. 800402-12-4 ]

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2D
Chemical Structure| 800402-12-4
Chemical Structure| 800402-12-4
Structure of 800402-12-4

Quality Control of [ 800402-12-4 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 800402-12-4 ]

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Product Details of [ 800402-12-4 ]

CAS No. :800402-12-4MDL No. :MFCD09834661
Formula :C5H4ClIN2Boiling Point :367.8°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :254.46Pubchem ID :45480366
Synonyms :

Computed Properties of [ 800402-12-4 ]

TPSA : 38.9 H-Bond Acceptor Count : 2
XLogP3 : 1.8 H-Bond Donor Count : 1
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 800402-12-4 ]

Signal Word:WarningClassN/A
Precautionary Statements:P305 P351 P338UN#:N/A
Hazard Statements:H302-H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 800402-12-4 ]

  • Upstream synthesis route of [ 800402-12-4 ]

[ 800402-12-4 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 14432-12-3 ]
  • [ 800402-12-4 ]
YieldReaction ConditionsOperation in experiment
78.1% With N-iodo-succinimide In acetonitrile at 70℃; for 16.00 h; Inert atmosphere Under nitrogen atmosphere, mixture of 2-chloro-4-aminopyridine (15 g, 0.116 mol, 1 eq) was dissolved in acetonitrile (200 ml), was heated in an oil bath to 70°C, was slowly added NIS (33 g, 0.139 mol, 1.2 eq.), stirred for 16 hours. Cooled to room temperature, saturated aqueous sodium carbonate was added and the reaction member system PH value was adjusted to 9-10, ethyl acetate (500 ml) and extracted. The organic phase was separated and washed with saturated washed twice with brine (100 ml), dried over anhydrous sodium sulfate, and concentrated in vacuo to give 2-chloro-4-amino-5-iodopyridine (23 g, yield: 78.1 percent).
45% With potassium acetate; Iodine monochloride In acetic acid for 4.00 h; Reflux To 2-chloro-4-amino pyridine (33 g, 1 eq), in a 2-neck 2 L round bottomed flask, acetic acid (1.5 L) was added and stirred for 10 min. To this mixture, potassium acetate (50 g, 2 eq) was added and stirred for 10 min. Iodine monochloride (50 g, 1.2 eq) was added slowly to the mixture and the contents refluxed at 120°C for 4 h while monitoring by TLC. After completion, the acetic acid was distilled off under vacuum and the residue was basified with NaHC03 and poured into water. The aqueous mixture was extracted with EtOAc (2 x 500 mL) and the organic layer was dried over anhydrous sodium sulphate, filtered and concentrated to obtain crude product. The crude was purified by column chromatography (silica gel, 60-120) using EtOAc in hexane as the eluent. The desired product eluted at 10percent EtOAc in hexane. The fractions with product were concentrated to obtain product 2-chloro-5-iodopyridin-4-amine as white solid (23 g, 45percent). 1H NMR (DMSO-d6, 400 MHz): δ 8.190 (s, 1H), 6.625 (s, 1H), 6.517 (brs, 2H).
40% at 70℃; 2-Chloro-pyridin-4-ylamine 1b* (3.2 g, 0.025 mol) and sodium acetate (4.1 g, 0.05 mol) were stirred in acetic acid (20 ml). A solution of iodine monochloride (4.1 g, 0.025 mol) in acetic acid (10 ml) was added and the reaction mixture was heated to 70 °C for approximately 3 h (NB: solution at -50 °C, brown colour faded and precipitate formed as the reaction proceeded). The reaction mixture was cooled to room temperature, then poured onto water (700 ml), and extracted with EtOAc. The organic layer was carefully washed with a solution of Na2CO3 followed by a solution of Na2S2O3, dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography using 10percent EtOAc in DCM to yield 2-chloro-5-iodo-pyridin-4-ylamine 2b* (2.60 g, 40percent). 1H NMR (400 MHz, CDCl3) δ (ppm): 8.34 (1 H, s), 6.63 (1 H, s), 4.78 (2 H, s).
40% With sodium acetate; Iodine monochloride In acetic acid at 70℃; for 3.00 h; 10.1
Synthesis of 2-chloro-5-iodo-pyridin-4-ylamine 2b*
2-Chloro-pyridin-4-ylamine 1b* (3.2 g, 0.025 mol) and sodium acetate (4.1 g, 0.05 mol) were stirred in acetic acid (20 mL).
A solution of iodine monochloride (4.1 g, 0.025 mol) in acetic acid (10 mL) was added and the reaction mixture was heated to 70 °C for approximately 3 h (NB: solution at ∼50 °C, brown colour faded and precipitate formed as the reaction proceeded).
The reaction mixture was cooled to room temperature, then poured onto water (700 mL), and extracted with EtOAc.
The organic layer was carefully washed with a solution of Na2CO3 followed by a solution of Na2S2O3, dried over MgSO4 and concentrated in vacuo.
The crude product was purified by column chromatography using 10 percent EtOAc in DCM to yield 2-chloro-5-iodo-pyridin-4-ylamine 2b* (2.60 g, 40 percent).
1H NMR (400 MHz, CDCl3) δ(ppm): 8.34 (1 H, s), 6.63 (1 H, s), 4.78 (2 H, s).
40% With potassium acetate; Iodine monochloride In acetic acid for 4.00 h; Heating / reflux Iodine monochloride (0.758 g, 4.67 mmol) was added to a solution of 2-chloro-4-amino pyridine (0.500 g, 3.89 mmol) and potassium acetate (0.763 g, 7.78 mmol) in acetic acid (30 ml_). The reaction mixture was heated under reflux for 4 hr. The solvent was removed in vacuo and the residue was partitioned between aqueous sodium hydrogenocarbonate (50 ml.) and ethyl acetate (50 ml_). The organic phase was dried (MgSO4) and the solvent was removed in vacuo. The crude product was purified by flash silica chromatography, eluting with ethyl acetate and hexane (1 / 9), to give the title compound as a pink solid (0.394 g, 40percent).1H NMR (CDCI3, 500 MHz) δ 8.33 (s, 1H), 6.63 (s, 1H), 4.85 (brs, 2H). LCMS (4) R, 1.66 min; m/z (ESI+) 254 [MH+].
39% With N-iodo-succinimide In N,N-dimethyl-formamide at 80℃; for 3.00 h; To a stirred solution of 2-chloropyridin-4-amine (5 g, 39 mmol) in DMF (50 mL)was added NIS (8.75 g, 39 mmol). The reaction mixture was then heated at 80 °C for 3 h.The mixture was cooled and the DMF removed in vacuo. The residue was partitionedbetween EtOAc and water and the layers were separated. The organic layer was dried over Na2SO4, filtered, and concentrated. The product was purified via column chromatography (10percent EtOAc/pet ether) to afford 2-chloro-5-iodopyridin-4-amine (4 g, 39percent yield). ‘H NIVIR (400MHz, DMSO-d6) ö 8.20 (s, 1H), 6.64 (s, 1H), 6.50 (br s, 2H); LC/MS: 254.8 (Mj. Further elution with 12percent EtOAc/pet ether afforded 2-chloro-3- iodopyridin-4-amine (4 g, 39percent yield).
38% With N-iodo-succinimide In N,N-dimethyl-formamide at 60 - 80℃; N-iodosuccinimide (15.75 g, 70 mmol) was added to a solution of 2-chloropyridin-4-amine (9.00 g, 70 mmol) in N,N'-dimethylformamide (140 mL) and the mixture was stirred at 80 °C for 6 hours.
Further N-iodosuccinimide (7.80 g, 35 mmol) was added and the mixture was stirred at 60 °C overnight.
After cooling to room temperature, the solvent was evaporated under reduced pressure and the residue was partitioned between water and ethyl acetate.
The organic layer was washed with a saturated aqueous solution of sodium thiosulphate, water and brine, dried (MgSO4) and concentrated.
The residue was purified by flash chromatography (6:1 to 2:1 hexanes/ethyl acetate) to yield the title compound (6.80 g, 38percent) as a beige solid.
LRMS (m/z): 255 (M+1)+.
1H-NMR δ (CDCl3): 4.77 (brs, 2H), 6.63 (s, 1H), 8.34 (s, 1H).
36% With N-iodo-succinimide In acetonitrileReflux N-lodosuccinimide (24.75 g, 110.0 mmol) was added to a solution of 2-chloro-pyridin-4-ylamine (12.85 g, 100.0 mmol) in acetonitrile (400 mL) and the mixture stirred and held at reflux overnight. Upon cooling to room temperature the solvent was removed in vacuo and residue partitioned between EtOAc (250 mL), saturated sodium thiosulfate (100 mL) andwater (250 mL). The organic layer was separated, washed with water (2 >< 250 mL), separated and the solvent removed in vacuo to afford an orange oil that was subjected to column chromatography on silica. Gradient elution with 30-50percent EtOAc in petrol afforded a pale orange solid that was rinsed with 25percent EtOAc in petrol (80 mL). Solids were collected by filtration and sucked dry to afford the title compound (7.32 g) as an off-white solid. Themother liquors were concentrated to dryness in vacuo and the residues subjected to columnchromatography on silica. Elution with 30-50percent EtOAc in petrol afforded further pure material(1.90 g). Combined yield: (9.22 g, 36percent) 1H NMR (DMSO-d6) 8.20 (1H, 5), 6.64 (1H, 5), 6.50(2H, br 5). MS: [M+H] 255.
36% With N-iodo-succinimide In acetonitrileReflux Preparation 10: 2-Chloro-5-iodo-pyridin-4-ylamineN-lodosuccinimide (24.75 g, 110.0 mmol) was added to a solution of 2-chloro-pyridin-4-ylamine(12.85 g, 100.0 mmol) in acetonitrile (400 mL) and the mixture stirred and held at refluxovernight. Upon cooling to room temperature the solvent was removed in vacuo and residuepartitioned between EtOAc (250 mL), saturated sodium thiosulfate (100 mL) and water (250 mL). The organic layer was separated, washed with water (2 >< 250 mL), separated and the solvent removed in vacuo to afford an orange oil that was subjected to column chromatography on silica. Gradient elution with 30-50percent EtOAc in petrol afforded a pale orange solid that was rinsed with 25percent EtOAc in petrol (80 mL). Solids were collected by filtration and sucked dry to afford the title compound (7.32 g) as an off-white solid. The mother liquors were concentrated to dryness invacuo and the residues subjected to column chromatography on silica. Elution with 30-50percent EtOAc in petrol afforded further pure material (1.90 g). Combined yield : (9.22 g, 36percent) 1H NMR (DMSO-d6) 8.20 (1 H, 5), 6.64 (1 H, 5), 6.50 (2H, br 5). MS: [M+H] 255.
36% With N-iodo-succinimide In acetonitrileReflux Preparation 7: 2-Chloro-5-iodo-pyridin-4-ylamine N-lodosuccinimide (24.75 g, 110.0 mmol) was added to a solution of 2-chloro-pyridin-4-ylamine (12.85 g, 100.0 mmol) in acetonitrile (400 mL) and the mixture stirred and held at reflux overnight. Upon cooling to room temperature the solvent was removed in vacuo and residue partitioned between EtOAc (250 mL), saturated sodium thiosulfate (100 mL) andwater (250 mL). The organic layer was separated, washed with water (2 >< 250 mL), separated and the solvent removed in vacuo to afford an orange oil that was subjected to column chromatography on silica. Gradient elution with 30-50percent EtOAc in petrol afforded a pale orange solid that was rinsed with 25percent EtOAc in petrol (80 mL). Solids were collected by filtration and sucked dry to afford the title compound (7.32 g) as an off-white solid. Themother liquors were concentrated to dryness in vacuo and the residues subjected to columnchromatography on silica. Elution with 30-50percent EtOAc in petrol afforded further pure material(1.90 g). Combined yield : (9.22 g, 36percent) 1H NMR (DMSO-d6) 8.20 (1H, 5), 6.64 (1H, 5), 6.50(2H, br 5). MS: [M+H] 255.
36% With N-iodo-succinimide In acetonitrile at 82℃; NIS (24.75 g, 110.0 mmol) was added to a solution of 2-chloropyridin-4-ylamine (12.85 g, 100.0 mmol) in MeCN (400 mL),and the mixture was stirred and held at reflux overnight. Uponcooling to r.t. the solvent was removed in vacuo and the residuepartitioned between EtOAc (250 mL), sat. Na2S2O3 (100 mL), andH2O (250 mL). The organic layer was separated, washed withH2O (2 × 250 mL), separated, and the solvent removed in vacuoto afford an orange oil that was subjected to column chromatographyon silica gel. Elution with 30–50percent EtOAc in PE afforded apale orange solid that was rinsed with 25percent EtOAc in PE (80 mL).The solids were collected by filtration and sucked dry to afford2-chloro-5-iodopyridin-4-ylamine (7.32 g) as an off-white solid.The mother liquors were concentrated to dryness in vacuo andthe residues subjected to column chromatography on silica.Elution with 30–50percent EtOAc in PE afforded further pure material(1.90 g). Combined yield 9.22 g, 36percent. 1H NMR (400 MHz, DMSOd6):δ = 8.20 (s, 1 H), 6.64 (s, 1 H), 6.50 (br s, 2 H). MS: m/z = 255,257 [M + H]+.
28.2% at 70℃; for 20.00 h; To a solution of 17.3 (5.0 g, 54.6 mmol,) in acetic acid (10 ml) was added sodium acetate (8.938 g, 109.0 mmol, 2.0 eq) and iodine monochloride (4.069 g, 65.5 mmol, 1.2 eq). Reaction mixture was heated at 70° C. for 20 hours. After completion of the reaction, mixture was concentrated under reduced pressure and residue was diluted with water and basified with sodium bicarbonate solution. Compound was extracted in EtOAc and washed with brine. Organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure to afford crude material which was purified by chromatography using 12percent to afford pure 17.4 (2.8 g, 28.2percent), m/z=255.1 [M+H]+.

Reference: [1] Patent: CN105622638, 2016, A. Location in patent: Paragraph 0194
[2] Patent: WO2015/38417, 2015, A1. Location in patent: Page/Page column 73; 74
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 10229 - 10240
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 11, p. 5221 - 5237
[5] Patent: WO2014/207260, 2014, A1. Location in patent: Page/Page column 77
[6] Patent: EP2818472, 2014, A1. Location in patent: Paragraph 0089
[7] Patent: WO2009/44162, 2009, A1. Location in patent: Page/Page column 237
[8] Patent: WO2016/210037, 2016, A1. Location in patent: Page/Page column 36; 37
[9] Patent: EP2108641, 2009, A1. Location in patent: Page/Page column 49
[10] Patent: WO2014/60768, 2014, A1. Location in patent: Page/Page column 93
[11] Patent: WO2014/60767, 2014, A1. Location in patent: Page/Page column 105; 106
[12] Patent: WO2014/60770, 2014, A1. Location in patent: Page/Page column 124
[13] Synlett, 2015, vol. 26, # 18, p. 2570 - 2574
[14] Patent: US2016/251376, 2016, A1. Location in patent: Paragraph 0477; 0480; 0481
[15] Patent: WO2006/59164, 2006, A2. Location in patent: Page/Page column 23-24
[16] Patent: WO2006/67532, 2006, A1. Location in patent: Page/Page column 18
[17] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 23, p. 7107 - 7112
[18] Patent: WO2010/130796, 2010, A1. Location in patent: Page/Page column 103-104
[19] Patent: WO2004/104001, 2004, A2. Location in patent: Page 74-75
  • 2
  • [ 14432-12-3 ]
  • [ 800402-12-4 ]
  • [ 909036-46-0 ]
YieldReaction ConditionsOperation in experiment
41% With sodium acetate; Iodine monochloride In acetic acid at 70℃; for 3.50 h; 4-Amino-2-chloro-5-iodopyridine (11); [00197] 4-Amino-2-chloropyridine (3.20 g 25 mmole) was stirred in acetic acid (20 mL) with sodium acetate (4.1 g 50 mmol) To the mixture was added a solution of iodine monochloride (4.1 g 25 mmol) in acetic acid (10 mL) and the reaction was heated at 70 °C for 3.5 h. Most of the acetic acid was evaporated and the reaction diluted with water (200 mL). The products were extracted with ethyl acetate (80, 70, 70 mL). The combined extracts were washed with 10percent sodium carbonate solution (100 mL), with 5percent sodium thiosulfate solution and with brine; then dried and evaporated. The crude product was purified by flash column chromatography on silica; eluting with 5percent ethyl acetate in dichloromethane, with 10percent ethyl acetate in dichloromethane and with 20percent ethyl acetate in dichloromethane to give first a small amount of di-iodinated product (618mg, 6.5percent); then the desired product 4-amino-5-iodo-2-chloropyridine (11 ) (2.64 g, 41 percent) and then the isomeric 4-amino-2-chloro-3-iodopyridine (12) (2.61 g, 41 percent). 4-Amino-5-iodo-2- chloropyridine (11 ) : 1 H-NMR (500 MHz, DMSO-d6): 6.48 (br s, 2H), 6.63 (s, 1 H), 8.19 (s, 1 H). 4-Amino-2-chloro-3-iodopyridine (12): 1 H-NMR (500MHz, DMSO-d6): 6.50 (br s, 2H), 6.54 (d, J= 5.36 Hz, 1 H); 7.74 (d, J= 5.68 Hz, 1 H).
41% at 70℃; for 3.50 h; 4-Amino-2-chloro-5-iodopyridine (11)
4-Amino-2-chloropyridine (3.20 g 25 mmole) was stirred in acetic acid (20 mL) with sodium acetate (4.1 g 50 mmol) To the mixture was added a solution of iodine monochloride (4.1 g 25 mmol) in acetic acid (10 mL) and the reaction was heated at 70° C. for 3.5 h.
Most of the acetic acid was evaporated and the reaction diluted with water (200 mL).
The products were extracted with ethyl acetate (80, 70, 70 mL).
The combined extracts were washed with 10percent sodium carbonate solution (100 mL), with 5percent sodium thiosulfate solution and with brine; then dried and evaporated. The crude product was purified by flash column chromatography on silica; eluting with 5percent ethyl acetate in dichloromethane, with 10percent ethyl acetate in dichloromethane and with 20percent ethyl acetate in dichloromethane to give first a small amount of di-iodinated product (618 mg, 6.5percent); then the desired product 4-amino-5-iodo-2-chloropyridine (11) (2.64 g, 41percent) and then the isomeric 4-amino-2-chloro-3-iodopyridine (12) (2.61 g, 41percent). 4-Amino-5-iodo-2-chloropyridine (11): 1H-NMR (500 MHz, DMSO-d6): 6.48 (br s, 2H), 6.63 (s, 1H), 8.19 (s, 1H). 4-Amino-2-chloro-3-iodopyridine (12): 1H-NMR (500 MHz, DMSO-d6): 6.50 (br s, 2H), 6.54 (d, J=5.36 Hz, 1H); 7.74 (d, J=5.68 Hz, 1H).
39% With N-iodo-succinimide In N,N-dimethyl-formamide at 80℃; for 3.00 h; Intermediate 252A: 2-chloro-5-iodopyridin-4-amine To a stirred solution of 2-chloropyridin-4-amine (5 g, 39 mmol) in DMF (50 mL) was added NIS (8.75 g, 39 mmol). The reaction mixture was then heated at 80 °C for 3 h. The mixture was cooled and the DMF removed in vacuo. The residue was partitioned between EtOAc and water and the layers were separated. The organic layer was dried over Na2S04, filtered, and concentrated. The product was purified via column chromatography (10percent EtO Ac/pet ether) to afford 2-chloro-5-iodopyridin-4-amine (4 g, 39percent yield). LCMS: 254.8 (M+). Further elution with 12percent EtO Ac/pet ether afforded 2- chloro-3-iodopyridin-4-amine (4 g, 39percent yield).
11.6 g at 80℃; for 3.00 h; 2-Chloro-4-aminopyridine (25 g, 194 mmol)And potassium acetate (19. 05 g, 194 mmol) were dissolved in 250 mL acetic acid and heated to 80 ° C. A solution of (31.56 g, 194 mmol) in acetic acid (40 mL) was added dropwise and the reaction mixture was stirred at 80 C for 3 h. The reaction mixture was cooled to room temperature and neutralized with saturated aqueous NaHC03 solution. A dark, off-white solid precipitated, which was dissolved in dichloromethane and washed with saturated aqueous NaHSO3, dried over Na2S04, concentrated and purified by column chromatography using hexane and ethyl acetate as eluents. 1. 6 g of the title compound were isolated,Along with 13. 4 g of the non-targeted isomer.

Reference: [1] Patent: WO2012/123745, 2012, A1. Location in patent: Page/Page column 67-68
[2] Patent: US2013/345181, 2013, A1. Location in patent: Page/Page column 0625; 0631
[3] Patent: WO2016/210034, 2016, A1. Location in patent: Page/Page column 171-172
[4] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 17, p. 4567 - 4570
[5] Patent: CN102449107, 2016, B. Location in patent: Paragraph 0318; 0319; 0320
  • 3
  • [ 14432-12-3 ]
  • [ 800402-12-4 ]
  • [ 909036-46-0 ]
  • [ 1171919-00-8 ]
YieldReaction ConditionsOperation in experiment
49.7% With potassium acetate; Iodine monochloride In acetic acid at 70℃; for 4.00 h; Inert atmosphere A mixture of 2-chloro-4-amino pyridine 1 (20g, 0.15mol), potassium acetate (22.9g, 0.23mol) and ICl (27.7g, 0.17mol) in glacial acetic acid (200mL) was heated to 70°C for 4h. The solvent was concentrated under reduced pressure. The residue was neutralized with 10percent NaHCO3 solution (250mL) and extracted with two 300-mL portions of EtOAc. The combined organic extracts were washed with brine (200mL) and dried over anhydrous Na2SO4. The solvent was removed in vacuum. The crude product showed a mixture of iodopyridines 2, 3 and 4 in the ratio 45:45:10. The required compound 2 (elution 2) was isolated via normal phase preparative HPLC (mobile phase: 60:40, 0.1percent TFA in hexane-IPA; column: SunFire Silica 19*150mm, 5μm; Flow rate: 18.0mL/min) in 49.7percent yield (19.7g) as an off white solid.
49.7% at 70℃; for 4.00 h; Inert atmosphere A mixture of 2-chloro-4-amino pyridine 1 (20g, 0.15mol), potassium acetate (22.9g, 0.23mol) and ICl (27.7g, 0.17mol) in glacial acetic acid (200mL) was heated to 70°C for 4h. After completion of the reaction, the solvent was concentrated under reduced pressure. The residue was neutralized with 10percent NaHCO3 solution (250mL) and extracted with two 300-mL portions of EtOAc. The combined organic extracts were washed with brine (200mL) and dried over anhydrous Na2SO4. The solvent was removed in vacuum. The crude product showed a mixture of iodopyridines 2, 3 and 4 in the ratio 45:45:10. The required compound 2 (elution 3) was isolated via normal phase preparative HPLC (mobile phase: 60:40, 0.1percent TFA in hexane-IPA; column: SunFire Silica 19×150mm, 5μm; Flow rate: 18.0mL/min) in 49.7percent yield (19.7g) as an off white solid; mp 102.9–104.1°C; 1H NMR (400MHz, DMSO-D6): δ 7.73 (d, J=4.0Hz, 1H), 6.52 (d, J=4.0Hz, 1H), 6.50 (s, 2H); MS (m/z): 255.0 [M+H]+. Anal. calcd. for C5H4ClIN2: C, 23.60; H, 1.58; N, 11.01; found: C, 23.59; H, 1.578; N, 10.99
Reference: [1] European Journal of Medicinal Chemistry, 2014, vol. 77, p. 288 - 297
[2] Journal of Molecular Structure, 2014, vol. 1081, p. 85 - 95
[3] Journal of Organic Chemistry, 2012, vol. 77, # 11, p. 5006 - 5016
[4] European Journal of Medicinal Chemistry, 2017, vol. 131, p. 275 - 288
  • 4
  • [ 657408-07-6 ]
  • [ 1251041-55-0 ]
  • [ 98-80-6 ]
  • [ 800402-12-4 ]
Reference: [1] Patent: US2012/61654, 2012, A1
  • 5
  • [ 14432-12-3 ]
  • [ 800402-12-4 ]
  • [ 1171919-00-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9382 - 9394
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