173282-69-4|6-Phenoxynicotinaldehyde| Ambeed

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Quality Control of [ 173282-69-4 ] Purity: 95% SDS Specification

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Product Details of [ 173282-69-4 ]

CAS No. :	173282-69-4
Formula :	C₁₂H₉NO₂
M.W :	199.21
SMILES Code :	O=CC1=CN=C(OC2=CC=CC=C2)C=C1
MDL No. :	MFCD02681950
InChI Key :	SOPOQXNWJNVZMI-UHFFFAOYSA-N
Pubchem ID :	2776500

Safety of [ 173282-69-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 173282-69-4 ]

* 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 [ 173282-69-4 ]

[ 173282-69-4 ] Synthesis Path-Downstream 1~31

1
[ 3099-50-1 ]
[ 108-95-2 ]
[ 173282-69-4 ]
5-diphenoxymethyl-2-phenoxypyridine [ No CAS ]

References: [1]Tetrahedron,1995,vol. 51,p. 12791 - 12796.
[2]Tetrahedron,1995,vol. 51,p. 12791 - 12796.

2
[ 3731-38-2 ]
[ 173282-69-4 ]
2-[1-(6-Phenoxy-pyridin-3-yl)-meth-(Z)-ylidene]-1-aza-bicyclo[2.2.2]octan-3-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2073 - 2077.

3
[ 173282-69-4 ]
[ 955043-47-7 ]

Yield	Reaction Conditions	Operation in experiment
26%		(a) 4-[(6-Phenoxypyridin-3-yl)methyl] amino}- lH-imidazole-5-carboxamide; Triethylamine (0.47 mL, 3.38 mmol) was added to 5-aminoimidazole-4-carboxamide hydrochloride (0.50 g, 3.1 mmol) in anhydrous methanol (12 mL). The reaction mixture was stirred for 10 min and <strong>[173282-69-4]6-phenoxynicotinaldehyde</strong> (0.74 g, 3.7 mmol) and acetic acid (0.09 mL, 1.57 mmol) were added. The dark solution was stirred over night and sodium cyanoborohydride (0.23 g, 3.7 mmol) was added. More sodium cyanoborohydride (0.15 g,2.4 mmol) was added after 40 min and the mixture was stirred for another 3h. The reaction mixture was heated at 50 C for 3 h, sodium cyanoborohydride (0.15 g, 2.4 mmol) was added and the mixture was heated at 50 C over night. Sodium borohydride (0.12 g, 3.2 mmol) was added and the mixture was heated at 50 0C for 1 h, more sodium borohydride (0.15 g, 4.0 mmol) and NMP (1.0 mL) were added and the mixture was heated at 60 0C for3.5 h. After cooling, NaHCO3 (sat., 20 mL) was added and some of the methanol was removed in vacuo. The mixture was extracted with EtOAc, the organic phase was extracted with IN HCl (2x30 mL) and the acidic phase was made basic with 2N NaOH and was extracted with DCM. The organic phase was dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography on silica (0 to 10% MeOH in DCM + NH3) to yield 0.25 g (0.81 mmol, 26%) of a slightly green syrup. 1H NMR (CDCl3) δ ppm 7.98 (IH) 7.68 (IH) 7.38 (2H) 7.18 (IH) 7.09 (2H) 6.99 (IH) 6.86 (IH) 6.46 (IH) 5.95 (2H) 4.37 (2H); MS (ESI) m/z 308 (M-I).

References: [1]Patent: WO2007/120098,2007,A1 .Location in patent: Page/Page column 85.

4
[ 173282-69-4 ]
[ 852476-78-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2073 - 2077.

5
[ 173282-69-4 ]
(2S,3R)-2-(6-Phenoxy-pyridin-3-ylmethyl)-1-aza-bicyclo[2.2.2]octan-3-ol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2073 - 2077.

6
[ 173282-69-4 ]
(2S,3S)-2-(6-Phenoxy-pyridin-3-ylmethyl)-1-aza-bicyclo[2.2.2]octan-3-ol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2073 - 2077.

7
[ 173282-69-4 ]
(4-Bromo-phenyl)-carbamic acid (2S,3S)-2-(6-phenoxy-pyridin-3-ylmethyl)-1-aza-bicyclo[2.2.2]oct-3-yl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2073 - 2077.

8
(3R*)-1-butyl-2,5-dioxo-3-((1R*)-1-hydroxy-2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane. hydrochloride [ No CAS ]
[ 173282-69-4 ]
(3R)-1-butyl-2,5-dioxo-3-((1R)-1-hydroxy-2-methylpropyl)-9-(6-phenyloxypyridin-3-ylmethyl)-1,4,9-triazaspiro[5.5]undecane dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of the compound prepared in Reference example 15(120mg) in dimethylformamide(1ml) was added acetic acid(59µl). The reaction mixture was added sodium triacetoxyborohydride(146mg) and <strong>[173282-69-4]3-formyl-6-phenyloxypyridine</strong>(89mg). The reaction mixture was stirred overnight at room temperature. The reaction mixture was added methanol and concentrated. The obtained residue was purified by column chromatography on silica gel (ethyl acetate → chloroform:methanol = 25:1) and the obtained compound was conversed to hydrochloride salt by using a conventional method to give the title compound(118mg) having the following physical data. TLC:Rf 0.48(chloroform:methanol = 10:1); NMR(CD3OD): δ 8.35 (d, J = 2.1 Hz, 1H), 8.12 (dd, J = 8.7, 2.1 Hz, 1H), 7.49-7.40 (m, 2H), 7.27 (t, J = 7.8 Hz, 1H), 7.15 (d, J = 7.8 Hz, 2H), 7.06 (d, J = 8.7, 1H), 4.39 (s, 2H), 4.14 (d, J = 2.1 Hz, 1H), 4.07-3.93 (m, 1H), 3.82-3.67 (m, 1H), 3.58-3.40 (m, 3H), 3.30-3.15(m, 1H), 3.19 (dd, J = 9.6, 2.1 Hz, 1H), 2.60-2.28 (m, 3H), 2.18-2.05 (m, 1H), 2.05-1.90 (m, 1H), 1.80-1.55 (m, 1H), 1.50-1.25 (m, 3H), 0.99 (d, J = 6.6 Hz, 3H), 0.97 (d, J = 6.6 Hz, 3H), 0.95 (t, J = 7.2 Hz, 3H); Optical rotation:[α]D +10.8 (c 1.05, methanol, 24C); HPLC conditions column:CHIRALCEL OJ-R, 0.46×15cm, DAICEL, OJR0CD-JB026: flow rate:0.7ml/min; solvent A solution: 0.1M aqueous solution of potassium dihydrogen phosphate, B solution: acetonitrile (A: B = 76:24); UV: 225 nm; retention time: 11.53 min.
		To a solution of the compound prepared in Reference example 3 (120mg) in dimethylformamide (1ml) was added acetic acid (59µl). The reaction mixture was added sodium triacetoxyborohydride (146mg) and <strong>[173282-69-4]3-formyl-6-phenyloxypyridine</strong> (89mg). The reaction mixture was stirred overnight at room temperature. The reaction mixture was added methanol and concentrated. The obtained residue was purified by column chromatography on silica gel (ethyl acetate → chloroform:methanol = 25:1) and the obtained compound was conversed to hydrochloride salt by using a conventional method to give the title compound (118mg) having the following physical data. TLC:Rf 0.48 (chloroform: methanol = 10:1); NMR (CD3OD): δ 8.35 (d, J = 2.1 Hz, 1H), 8.12 (dd, J = 8.7, 2.1 Hz, 1H), 7.49-7.40 (m, 2H), 7.27 (t, J = 7.8 Hz, 1H), 7.15 (d, J = 7.8 Hz, 2H), 7.06 (d, J = 8.7, 1 H), 4.39 (s, 2H), 4.14 (d, J = 2.1 Hz, 1H), 4.07-3.93 (m, 1H), 3.82-3.67 (m, 1H), 3.58-3.40 (m, 3H), 3.30-3.15 (m, 1H), 3.19 (dd, J = 9.6, 2.1 Hz, 1H), 2.60-2.28 (m, 3H), 2.18-2.05 (m, 1H), 2.05-1.90 (m, 1H), 1.80-1.55 (m, 1H), 1.50-1.25 (m, 3H), 0.99 (d, J = 6.6 Hz, 3H), 0.97 (d, J = 6.6 Hz, 3H), 0.95 (t, J = 7.2 Hz, 3H); Optical rotation:[α]D +10.8 (c 1.05, methanol, 24C); HPLC conditions column:CHIRALCEL OJ-R, 0.46×15cm, DAICEL, OJR0CD-JB026: flow rate:0.7ml/min; solvent A solution: 0.1 M aqueous solution of potassium dihydrogen phosphate, B solution: acetonitrile (A:B = 76:24); UV: 225 nm; retention time: 11.53 min.

References: [1]Patent: EP1378509,2004,A1 .Location in patent: Page 294-295.
[2]Patent: EP1378510,2004,A1 .Location in patent: Page 37-38.

9
[ 75-52-5 ]
[ 173282-69-4 ]
C₁₃H₁₀N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium acetate; acetic acid; at 100℃; for 3h;	To a solution of 6-phenoxy-pyridine-3-carbaldehyde (1.12 g, 5.62 mmol) described in Manufacturing Example 40-1-2 in acetic acid (10 mL) were added nitromethane (1.52 mL, 28.1 mmol) and ammonium acetate (866 mg, 11.2 mmol) under nitrogen atmosphere, which was stirred for 3 hours at 100 C. After being cooled to room temperature, the reaction solution was partitioned into water and ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure. The resulting residue was dissolved in dimethyl sulfoxide (17 mL) and acetic acid (3 mL). Sodium borohydride (336 mg, 8.43 mmol) was added to this solution at room temperature while cooling appropriately, and stirred for 30 minutes at room temperature. The reaction solution was partitioned by addition of sodium hydrogencarbonate, water and ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:1) to obtain the title compound (753 mg, 55%). 1H-NMR Spectrum (CDCl3) δ (ppm): 3.28 (2H, t, J=7.1 Hz), 4.60 (2H, t, J=7.1 Hz), 6.88 (1H, d, J=8.8 Hz), 7.11-7.14 (2H, m), 7.20-7.24 (1H, m), 7.39-7.43 (2H, m), 7.55 (1H, ddd, J=0.37, 2.6, 8.4 Hz), 8.07 (1H, d, J=2.4 Hz).

References: [1]Patent: US2007/105904,2007,A1 .Location in patent: Page/Page column 86.

10
3-(5-Amino-1-pentanone-1-yl)pyridine dihydrochloride [ No CAS ]
[ 173282-69-4 ]
2-phenoxy-5-((2-(pyridin-3-yl)-5,6-dihydropyridin-3(4H)-ylidene)methyl)pyridine dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	In isopropyl alcohol; at 80℃;	Example 34: Synthesis of 2-phenoxy-5-f(2-(pyridin-3-vD-5.6-dihydropyridin- 3f4H)-yIidene>rnethyl')pyridine dihydrochloride.; 3-(5-Ammoniopentanoyl)pyridinium chloride (101 mg, 0.40 mmol) and 6- pheϖoxynicotinaldehyde (120 mg, 0.60 mmol) were combined in a reaction vessel and treated with isopropanol (15 mL). The reaction vessel was sealed and the reaction was heated to 8O0C with stirring overnight. The reaction was then cooled to room temperature. The precipitate that formed was recovered by vacuum filtration and washed with a 20% solution of isopropanoi in hexane and then with ether. The recovered solid was then dried under vacuum giving 122 mg (73%) of a pale yellow solid. LC-MS: RT = 5.08 min, [M+H]+ = 342.1.

References: [1]Patent: WO2007/89626,2007,A2 .Location in patent: Page/Page column 55-56.

11
[ 870062-30-9 ]
[ 173282-69-4 ]
C₂₅H₂₇N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In methanol; at 50℃; for 0.333333h;pH 4.5 - 5;	6-Phenoxynicotinaldehyde (0.054 g, 0.272 mmol) and Intermediate D (0.100 g, 0.406 mmol) were allowed to stir in 15 mL of MeOH. Glacial acetic acid was added via pipet until a pH of ~ 4.5-5.0 was reached. The reaction was allowed to stir and heat at 50 0C for twenty min. Sodium cyanoborohydride (0.014 g, 0.2 mmol) was added and the reaction was allowed to continue stirring and heating for 16 h. LC/MS monitoring of reaction indicated reaction completion. The reaction was quenched with 1 mL H2O and concentrated to dryness. The residue re-dissolved in methylene chloride and washed with Brine (3x15mL). The organic layer was dried over MgSO4 concentrated to dryness. Purification via SiO2 chromatography using a (9/0.9/0.1) mixture of (CH2CI2ZCH3OHZNH3OH) afforded 42 mgs (23%) of the desired target compound. 1H NMR (300 MHz, CDCl3) δ 8.13 (d, IH), 7.70 (m, IH), 7.39 (m, 2H), 7.18 (m, 4H), 6.87 (m, 4H), 4.32 (m, IH), 3.75 (d, 4H), 2.69 (m, 2H), 2.30 (m, 5H), 19.7 (m, 2H), 1.85 (m, 2H), 1.70 (bs, 2H).

References: [1]Patent: WO2007/78251,2007,A1 .Location in patent: Page/Page column 46-47.

12
[ 141-82-2 ]
[ 173282-69-4 ]
[ 258348-10-6 ]

Yield	Reaction Conditions	Operation in experiment
		5 g (25.1 mmol) of 6-phenoxy-pyridine-3-carbaldehyde were dissolved in 50 ml of pyridine, and 3.134 g (30.1 mmol) of malonic acid and 213 mg (2.5 mmol) of piperidine were added. The reaction mixture was boiled under reflux for 6 h. After cooling to room temperature, it was poured into a mixture of ice and concentrated hydrochloric acid. The precipitated product was isolated by filtration. Yield: 5.66 g. MS: m/e =242 (M+H)+

References: [1]Patent: EP1939181,2008,A1 .Location in patent: Page/Page column 46.

13
[ 33513-42-7 ]
[ 59717-96-3 ]
[ 173282-69-4 ]

Yield	Reaction Conditions	Operation in experiment
37%		Manufacturing Example 40-1-2 6-Phenoxy-pyridine-3-carbaldehyde; To a solution of 5-bromo-2-phenoxy-pyridine (3.85 g, 15.4 mmol) described in Manufacturing Example 40-1-1 in tetrahydrofuran (60 mL) was added n-butyl lithium (10.6 mL, 1.60 M hexane solution, 16.9 mmol) under nitrogen atmosphere at -78 C., which was stirred for 35 minutes at -78 C. N,N-Dimethylformamide (1.55 mL, 20.0 mmol) was then added to this reaction solution at -78 C., which was stirred for further 10 minutes at room temperature. After allowing to room temperature, the reaction solution was partitioned into water and ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=5:1) to obtain the title compound (1.12 g, 37%).1H-NMR Spectrum (CDCl3) δ (ppm): 7.04 (1H, d, J=8.6 Hz), 7.17 (2H, d, J=7.5 Hz), 7.26-7.31 (1H, m), 7.44-7.48 (2H, m), 8.19 (1H, dd, J=2.2, 8.6 Hz), 8.63 (1H, d, J=2.2 Hz), 9.99 (1H, s).
37%		To a solution of 5-bromo-2-phenoxy-pyridine (3.85 g, 15.4 mmol) described in Manufacturing Example 40-1-1 in tetrahydrofuran (60 mL) was added n-butyl lithium (10.6 mL, 1.60 M hexane solution, 16.9 mmol) under nitrogen atmosphere at -78 C., which was stirred for 35 minutes at -78 C. N,N-Dimethylformamide (1.55 mL, 20.0 mmol) was then added to this reaction solution at -78 C., which was stirred for further 10 minutes at room temperature. After allowing to room temperature, the reaction solution was partitioned into water and ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=5:1) to obtain the title compound (1.12 g, 37%). 1H-NMR Spectrum (CDCl3) δ (ppm): 7.04 (1H, d, J=8.6 Hz), 7.17 (2H, d, J=7.5 Hz), 7.26-7.31 (1H, m), 7.44-7.48 (2H, m), 8.19 (1H, dd, J=2.2, 8.6 Hz), 8.63 (1H, d, J=2.2 Hz), 9.99 (1H, s).

References: [1]Patent: US2009/82403,2009,A1 .Location in patent: Page/Page column 88.
[2]Patent: US2007/105904,2007,A1 .Location in patent: Page/Page column 86.

14
[ 75-52-5 ]
[ 173282-69-4 ]
[ 936342-69-7 ]

Yield	Reaction Conditions	Operation in experiment
55%		Manufacturing Example 40-1-3 5-(2-Nitro-ethyl)-2-phenoxy-pyridine; To a solution of 6-phenoxy-pyridine-3-carbaldehyde (1.12 g, 5.62 mmol) described in Manufacturing Example 40-1-2 in acetic acid (10 mL) were added nitromethane (1.52 mL, 28.1 mmol) and ammonium acetate (866 mg, 11.2 mmol) under nitrogen atmosphere, which was stirred for 3 hours at 100 C. After being cooled to room temperature, the reaction solution was partitioned into water and ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure. The resulting residue was dissolved in dimethyl sulfoxide (17 mL) and acetic acid (3 mL). Sodium borohydride (336 mg, 8.43 mmol) was added to this solution at room temperature while cooling appropriately, and stirred for 30 minutes at room temperature. The reaction solution was partitioned by addition of sodium hydrogencarbonate, water and ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:1) to obtain the title compound (753 mg, 55%).1H-NMR Spectrum (CDCl3) δ (ppm): 3.28 (2H, t, J=7.1 Hz), 4.60 (2H, t, J=7.1 Hz), 6.88 (1H, d, J=8.8 Hz), 7.11-7.14 (2H, m), 7.20-7.24 (1H, m), 7.39-7.43 (2H, m), 7.55 (1H, ddd, J=0.37, 2.6, 8.4 Hz), 8.07 (1H, d, J=2.4 Hz).

References: [1]Patent: US2009/82403,2009,A1 .Location in patent: Page/Page column 88.

15
C₂H₄O₂*C₂₄H₄₃N₄O₄Pol [ No CAS ]
[ 173282-69-4 ]
1-butyl-3-(cyclohexylmethyl)-9-[(6-phenoxypyridin-3-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 5208 - 5223.

16
[ 1198595-32-2 ]
[ 173282-69-4 ]
C₃₇H₄₁NO₃Si [ No CAS ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 6462 - 6465.

17
[ 23100-12-1 ]
[ 108-95-2 ]
[ 173282-69-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With caesium carbonate; copper(l) chloride; In N,N-dimethyl-formamide; at 100℃; for 10h;	To a stirred solution of 6-chloronicotinaldehyde (2.0 g, 14.1 mmol, 1.0 eq.) and phenol (1.32 g, 14.1 mmol, 1.0 eq.) in DMF (20 mL) was added Cs2CO3 (5.5 g, 16.9 mmol, 1.2 eq.) and CuCl (1.61 g, 16.9 mmol, 1.2 eq.). The resulting mixture heated at 100 C. for 10 h. Following this, reaction was allowed to cool to RT and filtered through celite pad, the celite pad washed with ethyl acetate and water. The aqueous layer was separated extracted using ethyl acetate (3×30 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated under vacuum to get the solid residue. The crude was purified by normal phase silica-gel column provided title compound (2.8 g, 99%). LCMS: 200.0 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 9.99 (s, 1H) 8.70 (d, J=2.19 Hz, 1H) 8.27 (dd, J=8.55, 2.41 Hz, 1H) 7.43-7.52 (m, 2H) 7.18-7.32 (m, 4H)
92%	With caesium carbonate; copper(l) chloride; In N,N-dimethyl-formamide; for 10h;Reflux;	To a solution of 6-chloronicotinaldehyde (3) (0.28 g, 2 mmol) and phenol (0.19 g, 2 mmol) in DMF (30 mL) was added Cs2CO3 (0.78 g, 2.4 mmol) and CuCl (0.24 g, 2.4 mmol), then the mixture was refluxed for 10 h and then cooled to room temperature. The mixture was extracted with EtOAc, and the extract was washed successively with water and brine, and dried over anhydrous Na2SO4. The crude product was purified by recrystallization using methanol to give compound 4 as a white solid (0.36 g, 92%); mp = 91-93 C; 1H NMR (400 MHz, CDCl3): δ 9.98 (s, 1H, CHO), 8.63 (s, 1H, Py-H), 8.19 (d, J = 8.4 Hz, 1H, Py-H), 7.46 (t, J = 7.6 Hz, 2H, Ar-H), 7.30 (d, J = 7.6 Hz, 1H, Ar-H), 7.17 (d, J = 7.6 Hz, 2H, Ar-H), 7.16 (d, J = 8.4 Hz, 1H, Py-H); 13C NMR (100 MHz, CDCl3) δ 189.4, 167.3, 153.0, 152.8, 138.7, 129.9, 127.7, 125.8, 121.6, 112.1. ESI-HRMS (m/z): Calcd for C12H10NO2 [M+H]+ 200.0706. Found 200.0708.
92%	With caesium carbonate; copper(l) chloride; In N,N-dimethyl-formamide; for 10h;Reflux;	6-chloropyridine-3-carbaldehyde (2) (0.28 g, 2 mmol),Phenol (0.I9 g, 2 mmol) was dissolved in DMF (30 mL).Then Cs2CO3 (0.78 g, 2.4 mmol) and CuCl (0.24 g, 2.4 mmol) were added.It was then heated to reflux for 10 hours. Add ethyl acetate and water,Wash the organic phase with saturated brine, dry over anhydrous sodium sulfate, and dissolve.Recrystallization from methanol gave 0.36 g of a white solid.Yield 92%.

1.38 g

With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; for 0.5h;Microwave irradiation;

6-Chloro-pyridine-3-carbaldehyde (1.50 g; 10.6 mmol) and Phenol (1.20 g; 12.7 mmol) were dissolved in DMF (10 ml) in a microwave vial; K2CO3 (2.20 g; 15.9 mmol) was added and the reaction mixture was stirred at 110 C. during 30 minutes. The reaction mixture was diluted with water (50 ml) and the obtained precipitate was filtered off, washed with water and dried in the air. Obtained 1.38 g of the desired compound. (0290) Example 5p: HPLC-MS (Method): Z017_S04 Rt [min]: 0.93 MS: 200 [M+H]+

References: [1]Patent: US2020/206233,2020,A1 .Location in patent: Paragraph 0456-0457.
[2]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 391 - 402.
[3]Patent: CN104892577,2018,B .Location in patent: Sheet 0031; 0032; 0033; 0034.
[4]Patent: US2020/123141,2020,A1 .Location in patent: Paragraph 0288-0290.

18
[ 173282-69-4 ]
[ 123313-07-5 ]
(E)-6-methyl-4-((6-phenoxypyridin-3-yl)methyleneamino)-4,5-dihydro-1,2,4-triazin-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With toluene-4-sulfonic acid; In methanol; for 6h;Reflux;	To a solution of 1 (0.51 g, 4.00 mmol) and <strong>[173282-69-4]6-phenoxynicotinaldehyde</strong> (4) (0.80 g, 4.00 mmol) in methanol (50 mL) was added p-toluene sulfonic acid (0.14 g, 0.80 mmol), and then the mixture was refluxed for 6 h. The solution was cooled and then concentrated under reduced pressure. The crude product was purified by recrystallization using methanol to give compound II as a white solid (0.80 g, 65%); mp = 200-201 C; 1H NMR (400 MHz, DMSO-d6): δ 10.10 (s, 1H, NH), 8.37 (s, 1H, N=CH), 8.20 (d, J = 8.8 Hz, 1H, Py-H), 7.89 (s, 1H, Py-H), 7.44 (t, J = 7.6 Hz, 2H, Ar-H), 7.24 (t, J = 7.6 Hz, 1H, Ar-H), 7.17 (d, J = 7.6 Hz, 2H, Ar-H), 7.11 (d, J = 8.8 Hz, 1H, Py-H), 4.35 (s, 2H, CH2), 1.94 (s, 3H, CH3); 13C NMR (100 MHz, DMSO-d6) δ 163.6, 153.6, 147.3, 146.9, 144.0, 137.8, 136.8, 129.8, 126.7, 124.9, 121.4, 111.9, 47.7, 20.2. ESI-HRMS (m/z): Calcd for C16H16N5O2 [M+H]+ 310.1299. Found 310.1300.
65%	With toluene-4-sulfonic acid; for 6h;Reflux;	In a 250 mL single-mouth bottle, add aminotriazinone (I) (0.5I g, 4 mmol),P-toluenesulfonic acid (0.I4 g, 0.8 mmol) and methanol (I20 mL) were stirred and dissolved.Then 6-phenoxypyridine-3-carbaldehyde (3) (0.80 g, 4 mmol) was added and heated to reflux for 6 h.The reaction was monitored by TLC. After the reaction solution is decomposed under reduced pressure,Recrystallization from methanol gave 0.80 g of a white solid.Yield 65%.

References: [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 391 - 402.
[2]Patent: CN104892577,2018,B .Location in patent: Paragraph 0031; 0032; 0035; 0036.

19
[ 20099-89-2 ]
[ 1366060-25-4 ]
[ 57-13-6 ]
[ 173282-69-4 ]
[ 1426389-59-4 ]

Yield	Reaction Conditions	Operation in experiment
33%		General procedure: Reaction mixtures of ketal-protected thioamide 3 (50 mg,0.246 mmol, 1 equiv) and a-bromoketones 4 (0.246 mmol) wereprepared in 0.6 mL of DMF and heated to 150 C for 5 min in sealedvials. After cooling, aldehydes 5 (0.295 mmol, 1.2 equiv) and ureas6 (0.295 mmol, 1.2 equiv) were added and the reaction mixturesheated to 200 C for an additional 10 min. Once cooled, the crudereaction mixtures were purified using reverse-phase preparativeHPLC, lyophilized, and tested for anti-HIV activity. When measuringthe efficiency of the process, the crude reaction mixtures wereadsorbed onto silica gel, loaded onto a pre-packed silica gel column(12 g), and chromatographed using either hexanes:EtOAc or CH2-Cl2:MeOH.

References: [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 6248 - 6265.

20
1,3-dioxohexahydroimidazo[1,5-a]pyrazin-2(3H)-yl 2,3-dihydro-4H-benzo[b][1,4]oxazine-4-carboxylate [ No CAS ]
[ 173282-69-4 ]
1,3-dioxo-7-((6-phenoxypyridin-3-yl)methyl)hexahydroimidazo[1,5-a]pyrazin-2(3H)-yl 2,3-dihydro-4H-benzo[b][1,4]oxazine-4-carboxylate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 563 - 568.

21
C₆H₁₂N₂O₂ [ No CAS ]
[ 173282-69-4 ]
C₁₈H₂₁N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
140 mg		Example 36 was synthesised in analogy to example 31. (0376) Starting materials: Example 5p (120 mg; 0.60 mmol) and Example 1a (95.5 mg; 0.66 mmol). The mixture was stirred at room temperature during 18 hours. The crude was purified by preparative HPLC. Obtained 140 mg of the desired compound. (0377) Example 36 HPLC-MS ; Method: Z011_S03; Rt [min]: 0.88 MS: 328 [M+H]+ Rt [min]: 2.73; Chiral SFC Method:: I_SA_20_IPA_NH3_001 e.e.:100% 1H NMR (400 MHz, DMSO-d6); δ ppm: 1.90 (m, 1H); 2.11 (m, 1H); 2.57 (m, 3H); 2.61-2.67 (m, 1H); 2.90 (m, 1H); 3.43-3.60 (m, 3H); 3.83-3.89 (m, 2H); 6.99 (d, J=8.37 Hz, 1H); 7.10-7.23 (m, 3H); 7.41 (t, J=7.53 Hz, 2H); 7.62-7.71 (m, 1H); 7.78 (dd, J=8.40, 2.41 Hz, 1H); 8.04 (d, J=2.36 Hz, 1H).

References: [1]Patent: US2020/123141,2020,A1 .Location in patent: Paragraph 0352-0355; 0370-0373.

22
[ 173282-69-4 ]
[ 343338-28-3 ]
(R,E)-2-methyl-N-((6-phenoxypyridin-3-yl)methylene)propane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(II) sulfate; In 1,2-dichloro-ethane; at 20 - 80℃; for 16h;	To a stirred solution of <strong>[173282-69-4]6-phenoxynicotinaldehyde</strong> (1.5 g, 7.5 mmol, 1.0 eq.) and Copper(II) sulfate (2.9 g, 18.8 mmol, 2.5 eq.) in dichloroethane (10 mL) was added (R)-2-methylpropane-2-sulfinamide (1.3 g, 11.2 mmol, 1.8 eq.) at RT. The resulting mixture was heated at 80 C. for 16 h. Following this, reaction was allowed to cool to room temperature, filtered through celite pad, the celite pad washed with dichloromethane (20 mL). The combined filtrate dried over anhydrous Na2SO4 and concentrated under vacuum to get the solid residue which was purified by normal phase silica-gel column chromatography to get the title compound (1.0 g, 44%). LCMS: 303.0 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.68 (d, J=2.19 Hz, 1H) 8.58 (s, 1H) 8.37 (dd, J=8.77, 2.19 Hz, 1H) 7.43-7.50 (m, 2H) 7.16-7.30 (m, 4H) 1.18 (s, 9H).

References: [1]Patent: US2020/206233,2020,A1 .Location in patent: Paragraph 0456; 0458.

23
[ 173282-69-4 ]
(R)-2-methyl-N-((S)-1-(6-phenoxypyridin-3-yl)ethyl)propane-2-sulfinamide [ No CAS ]

References: [1]Patent: US2020/206233,2020,A1 .

24
2-amino-1-(benzo[b]thiophen-2-yl)ethanol [ No CAS ]
[ 173282-69-4 ]
C₂₂H₁₈N₂O₂S [ No CAS ]