923169-37-3|4-(Hydroxymethyl)picolinic acid| Ambeed

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Quality Control of [ 923169-37-3 ] Purity: 98% SDS Specification

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Product Details of [ 923169-37-3 ]

CAS No. :	923169-37-3
Formula :	C₇H₇NO₃
M.W :	153.14
SMILES Code :	O=C(O)C1=NC=CC(CO)=C1
MDL No. :	MFCD08447083
InChI Key :	QMLYYPGJXCVEHA-UHFFFAOYSA-N
Pubchem ID :	22645434

Safety of [ 923169-37-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 923169-37-3 ]

* 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 [ 923169-37-3 ]

[ 923169-37-3 ] Synthesis Path-Downstream 1~35

1
[ 923169-37-3 ]
[ 1119492-95-3 ]
bis(2-phenylpyridinato-N,C₂)-mono(4-[hydroxymethyl]-2-pyridine carboxylato-N,O)iridium(III) [ No CAS ]

References: [1]Organometallics,2009,vol. 28,p. 1082 - 1092.

2
[ 923169-37-3 ]
[ 1255305-41-9 ]
[ 1255304-34-7 ]

Yield	Reaction Conditions	Operation in experiment
62%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 21h;	To a solution of 3-[4-(4-cyclopropylbenzyloxy)-3-methoxyphenyl]azetidine monohydrochloride (5.0 g) prepared in (5), 4-hydroxymethylpyridine-2-calboxylic acid (2.2 g), WSC.HCl (3.3 g) and HOBt.H2O (2.7 g) in DMF (50 mL) was added triethylamine (3.0 mL). The reaction mixture was stirred at RT for 21 hr. Water was added to the reaction mixture and the mixture was extracted with a mixed solvent of ethyl acetate/THF. The organic layer was washed with water and aqueous 1 N NaOH, and then dried over MgSO4. The solvent was removed under reduced pressure. Hexane was added to the residue. The precipitated solid was collected on a filter and dried to give the title compound (4.0 g, 62%).1H-NMR (400 MHz, DMSO-d6) delta: 8.54 (1H, d, J=4.85 Hz), 7.95 (1H, s), 7.45-7.44 (1H, m), 7.30 (2H, d, J=8.16 Hz), 7.08 (2H, d, J=8.16 Hz), 6.99-6.97 (2H, m), 6.87 (1H, dd, J=8.38, 1.98 Hz), 5.52 (1H, t, J=5.84 Hz), 4.99 (2H, s), 4.97 (1H, t, J=9.26 Hz), 4.60 (2H, d, J=5.73 Hz), 4.55 (1H, dd, J=10.26, 6.29 Hz), 4.45 (1H, t, J=9.04 Hz), 4.08 (1H, dd, J=9.92, 6.62 Hz), 3.93-3.85 (1H, m), 3.77 (3H, s), 1.94-1.88 (1H, m), 0.96-0.92 (2H, m), 0.68-0.64 (2H, m).

References: [1]Patent: US2010/331301,2010,A1 .Location in patent: Page/Page column 24.

3
[ 923169-37-3 ]
4-(hydroxymethyl)-N,N-dimethylpicolinamide [ No CAS ]

References: [1]Patent: US2015/291549,2015,A1 .

4
[ 923169-37-3 ]
[ 124-40-3 ]
[ 332013-45-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; N,N-dimethyl-formamide; for 0.5h;	A solution of <strong>[923169-37-3]4-(hydroxymethyl)picolinic acid</strong> (0.100 g, 0.653 mmol) in N,N-dimethylformamide (2.0 mL) was treated with Hunig's Base (0.228 mL, 1.306 mmol) followed by dimethylamine, 2.0 M in THF (0.392 mL, 0.784 mmol) and HATU (0.323 g, 0.849 mmol). The reaction was stirred for 30 minutes. The product was purified by silica gel column chromatography (24 g SiO2, 0-10% (20 CV), 10-20% (2 CV), 20% (15 CV) methanol in dichloromethane) to afford the product (0.101 g, 0.560 mmol, 86% yield), as a viscous oil. LCMS (Condition MeOH-AA, ES+) M+H=181.1, 0.88 minutes, calculated exact mass=180.09.

References: [1]Patent: US2015/291549,2015,A1 .Location in patent: Paragraph 1154; 1155.

5
[ 923169-37-3 ]
C₇H₆N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Under argon, a stirred solution of appropriate carboxylic acid (0.37 mmol, 1.0 eq.) and Et3N (0.48 mmol, 1.3 eq.) in dry THF (7 mL) was cooled to -10 C. Ethyl chloroformate (0.55 mmol, 1.5 eq.) was dropwise added and the resulting mixture was stirred for 2 h. Afterward, a solution of sodium azide (0.63 mmol, 1.7 eq.) in water (2 mL) was added in one portion. After 1 h at -10 C, the reaction was found to be complete (TLC) and was quenched into iced water (5 mL). The mixture was extracted with EtOAc (3 * 10 mL) and the combined organic layers were successively dried over MgSO4, filtered and evaporated under reduced pressure. The crude acyl azide was placed in dry toluene (20 mL) and the mixture heated at reflux for 1 h to give the corresponding crude isocyanate. The latter was dissolved in dry dioxane (7 mL) prior to adding the amine 4 (0.37 mmol, 1.0 eq.). The solution was heated at reflux for 24 h. The reaction mixture was cooled to room temperature and the volatiles were removed to dryness in vacuum at 40 C. The dark residue was purified by silica gel chromatography column (CH2Cl2/MeOH 99/1) to afford the desired valmerins.

References: [1]European Journal of Medicinal Chemistry,2016,vol. 115,p. 311 - 325.

6
[ 923169-37-3 ]
C₇H₆N₂O₂ [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2016,vol. 115,p. 311 - 325.

7
[ 923169-37-3 ]
1-(4-(hydroxymethyl)pyridin-2-yl)-3-(6-oxo-1,2,3,4,6,10b-hexahydropyrido[2,1-a]isoindol-10-yl)urea [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2016,vol. 115,p. 311 - 325.

8
[ 923169-37-3 ]
1-[4-(fluoromethyl)pyridin-2-yl]-3-(6-oxo-1,2,3,4,6,10b-hexahydropyrido[2,1-a]isoindol-10-yl)urea [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2016,vol. 115,p. 311 - 325.

9
[ 67-56-1 ]
[ 923169-37-3 ]
[ 1206973-14-9 ]

Yield	Reaction Conditions	Operation in experiment
22 g	With thionyl chloride; In dichloromethane; at 0 - 20℃; for 3h;Inert atmosphere;	A reaction flask was charged with <strong>[923169-37-3]4-(hydroxymethyl)pyridine-2-carboxylic acid</strong> (145.8 mmol), methanol (150 mL) and DCM (150 mL) under argon, and SOCl2 (1.46 mol) was added dropwise at 0 C with stirring at 0 C. After stirring at room temperature for 3 hours, the solvent was evaporated under reduced pressure, EA (80 mL) and filtered to give 22 g of a white solid (Compound 32).

References: [1]Patent: CN106496107,2017,A .Location in patent: Paragraph 0182; 0183; 0184.

10
[ 923169-37-3 ]
[ 765-30-0 ]
[ 1353657-40-5 ]

Yield	Reaction Conditions	Operation in experiment
26 g		The reaction flask was charged with <strong>[923169-37-3]4-(hydroxymethyl)pyridine-2-carboxylic acid</strong> (145.8 mmol), DCM (200 mL) and 10 drops of DMF, and SOCl2 (1.75 mol) was added dropwise with stirring at 0 C. After stirring for 2 hours at room temperature, the solvent was evaporated under reduced pressure followed by the additiob of DCM (100 mL), TEA (40.5 mmol) and cyclopropylamine (175 mmol). The mixture was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure. EA was added dropwise to give a solid precipitate to give a total of 26 g of a white solid (Compound 33).

References: [1]Patent: CN106496107,2017,A .Location in patent: Paragraph 0185; 0186; 0187.

11
[ 923169-37-3 ]
(S)-N-(4-amino-2-hydroxybicyclo[2.2.2]octan-1-yl)-2-(4-chloro-3-fluorophenoxy)acetamide hydrochloric acid [ No CAS ]
N-{(3S)-4-[2-(4-chloro-3-fluorophenoxy)acetamido]-3-hydroxybicyclo[2.2.2]octan-1-yl}-4-(hydroxymethyl)pyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; for 2h;	A mixture of Example 473A (55.0 mg, 0.145 mmol), triethylamine (0.051 mL, 0.363 mmol), <strong>[923169-37-3]4-(hydroxymethyl)picolinic acid</strong> (28.9 mg, 0.189 mmol) and 1- [bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate, 71.7 mg, 0.189 mmol, HATU) in N,N-dimethylformamide (2 mL) was stirred for 2 hours. The reaction mixture was quenched with brine and saturated NaHCO3 and extracted with ethyl acetate (2×). The combined organic layers were concentrated, and the residue was purified by reverse-phase HPLC (see protocol in Example 273E) to provide the title compound (36.7 mg, 49%). 1H NMR (400 MHz, CD3OD) delta ppm 8.53 (d, J = 5.1 Hz, 1H), 8.07 (dd, J = 1.7, 0.9 Hz, 1H), 7.60- 7.50 (m, 1H), 7.37 (t, J = 8.8 Hz, 1H), 6.93 (dd, J = 10.9, 2.8 Hz, 1H), 6.82 (ddd, J = 8.9, 2.9, 1.3 Hz, 1H), 4.72 (t, J = 0.9 Hz, 2H), 4.51- 4.42 (m, 2H), 4.32 (ddd, J = 9.4, 3.3, 1.5 Hz, 1H), 2.70- 2.54 (m, 1H), 2.29- 1.89 (m, 9H); MS (ESI+) m/z 478.2 (M+H)+.

References: [1]Patent: WO2017/193063,2017,A1 .Location in patent: Page/Page column 549.

12
[ 923169-37-3 ]
[ 5970-45-6 ]
bis(4-(hydroxymethyl)picolinato-κ²N,O)zinc(II)-water [ No CAS ]

References: [1]New Journal of Chemistry,2018,vol. 42,p. 3619 - 3632.

13
[ 923169-37-3 ]
[ 1255305-42-0 ]

References: [1]Patent: US2010/331301,2010,A1 .

14
[ 923169-37-3 ]
[ 1255303-54-8 ]

References: [1]Patent: US2010/331301,2010,A1 .

15
[ 923169-37-3 ]
[ 1255305-43-1 ]

References: [1]Patent: US2010/331301,2010,A1 .

16
[ 923169-37-3 ]
[ 1255303-56-0 ]

References: [1]Patent: US2010/331301,2010,A1 .

17
[ 923169-37-3 ]
[ 1255305-46-4 ]

References: [1]Patent: US2010/331301,2010,A1 .

18
[ 923169-37-3 ]
5-[(3R)-piperidin-3-yl]methoxy}-2-(1H-pyrazol-5-yl)pyridine [ No CAS ]
C₂₁H₂₃N₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With propylphosphonic anhydride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	General procedure: N,N-Diisopropylethylamine (132 mL), 4-hydroxycyclohexane-1-carboxylic acid (33 mg) and propylphosphonicanhydride (1.6 mol/L N,N-dimethylformamide solution, 238 mL) were added to a solution of the compound (50 mg)obtained in Reference Example 14-1 in N,N-dimethylformamide (2 mL), and the mixture was stirred at room temperatureovernight. The mixture was purified by preparative LC-MS to give the title compound (Example 3-2) (25 mg) which wasa trans isomer as a highly polar compound, as a colorless amorphous substance.1H NMR (500 MHz, DMSO-d6) delta ppm 1.09 - 2.03 (m, 14.5 H) 2.85 - 2.98 (m, 0.5 H) 3.00 - 3.20 (m, 1.5 H) 3.21 - 3.40(m, 1 H) 3.78 - 4.08 (m, 3.5 H) 4.35 - 4.45 (m, 0.5 H) 4.48 - 4.58 (m, 1 H) 6.73 (s, 1 H) 7.36 - 7.96 (m, 3 H) 8.23 - 8.33 (m, 1 H).MS ESI/APCI Multi posi: 385 [M+H]+. The title compound (Example 3-3) (23.7 mg) which was a cis isomer as a less polar compound was obtainedas a colorless amorphous substance.1H NMR (600 MHz, DMSO-d6) delta ppm 1.13 - 2.02 (m, 12 H) 2.45 - 2.63 (m, 1.5 H) 2.84 - 2.95 (m, 0.5 H) 2.99 - 3.17 (m,1 H) 3.26 - 3.37 (m, 1 H) 3.71 - 4.09 (m, 4.5 H) 4.19 - 4.30 (m, 1 H) 4.38 - 4.46 (m, 0.5 H) 6.73 (br s, 1 H) 7.38 - 7.93(m, 3 H) 8.24 - 8.35 (m, 1 H). MS ESI/APCI Multi posi: 385 [M+H]+.

References: [1]Patent: EP3418276,2018,A1 .Location in patent: Paragraph 0763; 0764; 0765; 0766; 0767.

19
[ 923169-37-3 ]
methyl 4-((prop-2-ynyloxy)methyl)picolinate [ No CAS ]