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CAS No. : | 13538-42-6 | MDL No. : | MFCD03791262 |
Formula : | C6H7N3O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AGSDASDGMNDAIE-UHFFFAOYSA-N |
M.W : | 137.14 | Pubchem ID : | 351653 |
Synonyms : |
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Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P301+P310 | UN#: | 2811 |
Hazard Statements: | H301 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.9% | With ammonium hydroxide | |
With ammonium hydroxide | ||
Multi-step reaction with 3 steps 1: acetic acid 2: concentrated aqueous NH3 3: concentrated aqueous NH3 / 130 °C |
With ammonia In methanol at 60℃; | 22.1 2-amino-4-methoxycarbonylpyridine (1) (0.77 g, 5.1 mmol) was heated overnight with stirring at 60°C in a sealed system with ammonia methanol (7 N, 20 ml). After cooling to 23 °C the solvent was removed by rotary evaporator to give compound 2 (0.7 g). LCMS (APCI+) : 138. 2 [100 %]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; | <Example 117> 2-[2-(4-bromo-phenoxy)-acetylamino]-isonicotinainide <n="80"/>To solution of (4-bromo-phenoxy)-acetic acid(100 mg, 0.43 mmol), 2-amino isonicotinamide(89.39 mg, 0.65 mmol) and DMAP(106 mg, 0.86 mmol) in DMF 5 ml was added PyBOP(452 mg, 0.86 mmol), and stirred room temperature. Reaction mixture was poured onto ice cold water, diluted by methanol/MC mixture (10%). The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgStheta4, and concentrated. The residue was purified by PLC(EtoAC:Hexane:MeOH=3:6: 1-2:4:1) to afford 2-[2-(4-bromo-phenoxy)-ace1ylamino]-isonicotinamide as a colorless solid (0.083g, 55 % yield).1H NMR (DMSO-dfo 300 MHz) 10.72(1H5 s, CONH), 8.44(1H, d, J=3.0 Hz, CONH2), 8.40(1H, s, CONH2), 8.19(1H, brs, pyridine), 7.67(1H, brs, pyridine), 7.50-7.44(3H, m, pyridine, aromtic), 6.97-6.92(2H, m, aromatic), 4.83(2H, s, OCH2). |
55% | With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; | To solution of (4-bromo-phenoxy)-acetic acid (100 mg, 0.43 mmol), 2-amino isonicotinamide (89.39 mg, 0.65 mmol) and DMAP (106 mg, 0.86 mmol) in DMF 5 ml was added PyBOP (452 mg, 0.86 mmol), and stirred room temperature. Reaction mixture was poured onto ice cold water, diluted by methanol/MC mixture (10%). The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by PLC (EtoAC:Hexane:MeOH=3:6:1-2:4:1) to afford 2-[2-(4-bromo-phenoxy)-acetylamino]-isonicotinamide as a colorless solid (0.083 g, 55% yield). 1H NMR (DMSO-d6, 300 MHz) 10.72 (1H, s, CONH), 8.44 (1H, d, J=3.0 Hz, CONH2), 8.40 (1H, s, CONH2), 8.19 (1H, brs, pyridine), 7.67 (1H, brs, pyridine), 7.50-7.44 (3H, m, pyridine, aromatic), 6.97-6.92 (2H, m, aromatic), 4.83 (2H, s, OCH2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.5% | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide | 119 2-[2^44ert-bu1yl-phenoxy)-acetylamino]-isonicotinamide A solution of 4-tert-butylphenoxy acetic acid(60.1 mg, 0.29 mmol), 2-amino isonicotinatnide(60.3 mg,0.44 mmol), DBPEA(0.1 ml, 0.58 mmol) and PyBOP(301.8 mg, 0.58 mmol) in DMF 4.0 mL was stirred, then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by Prep-TLC(n-Hexane:EtoAc:MeOH=6:3:l) to give 2-[2-(44ert-butyl-phenoxy)-a∞tylarnino]-isonicotinamide as a white solid (53.6 mg, 56.5% yield).1H-NMR (DMSO-dfo 300 Hz) 10.64(1H, s, NH), 8.42-8.46(2H, m, aromatic-H), 8.20(1H, s, NH2), 7.68(1H, s, NH2), 7.49-7.51(1H, m, aromatic-H), 7.28-7.32(2H, m, aromatic-H), 6.86-6.91(2H, m, aromatic-H), 4.78(2H, s, CH2), 1.24 (9H, s, CH3). |
56.5% | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide | 119 2-[2-(4-tert-butyl-phenoxy)-acetylamino]-isonicotinamide A solution of 4-tert-butylphenoxy acetic acid (60.1 mg, 0.29 mmol), 2-amino isonicotinamide (60.3 mg, 0.44 mmol), DIPEA (0.1 ml, 0.58 mmol) and PyBOP (301.8 mg, 0.58 mmol) in DMF 4.0 mL was stirred, then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by Prep-TLC (n-Hexane:EtoAc:MeOH=6:3:1) to give 2-[2-(4-tert-butyl-phenoxy)-acetylamino]-isonicotinamide as a white solid (53.6 mg, 56.5% yield). 1H-NMR (DMSO-d6, 300 Hz) 10.64 (1H, s, NH), 8.42-8.46 (2H, m, aromatic-H), 8.20 (1H, s, NH2), 7.68 (1H, s, NH2), 7.49-7.51 (1H, m, aromatic-H), 7.28-7.32 (2H, m, aromatic-H), 6.86-6.91 (2H, m, aromatic-H), 4.78 (2H, s, CH2), 1.24 (9H, s, CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66.8% | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide | 120 2-(2-p-tolyloxy-acerylamino)-isonicotinamideA solution of 4 p-tolyloxy-acetic acid(60.1 mg, 0.36 mmol), 2-amino-isonicotinamide(74.1 mg, 0.54 mmol), DIPEA(0.12 ml, 0.72 mmol) and PyBOP(374.4 mg, 0.72 mmol) in DMF 5.0 mL was stirred, then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over anhydrousMgSO4, and concentrated. The residue was purified by Prep-TLC(CH2Cl2:Me0H= 10:1) to give 2-(2-p-tolyloxy- acetylamino)-isonicotinamide as a white solid (68.5 mg, 66.8% yield).1H-NMR (DMSO-dβ, 300 Hz) 10.61(1H, s, NH), 8.42-8.45(2H, m, aromatic-H), 8.20(1H, s, NH2), 7.68(1H, s, NH2), 7.49-7.51(1H, m, aromatic-H), 7.10 (2H, d, J=8.7 Hz, aromatic-H), 6.85-6.88(2H, m, aromatic- H), 4.76(2H, s, CH2), 2.23(3H, s, CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58.9% | With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; | 121 2-(2-phenoxy-acetylamino)-isonicotinamideTo solution of (phenoxy-acetic acid(100 mg, 0.65 minol), 2-amino isonicotinamide(180 mg, 1.31 mmol) and DMAP(160 mg, 1.31 mmol) in DMF 5 ml was added PyBOP(684 mg, 1.31 mmol), and stirred room temperature. Reaction mixture was poured onto ice cold water, diluted by methanol/MC mixture (10%). The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSθ4, and concentrated. The residue was purified by PLC(EtOAc:n-Hexanes:MeOH=l:2:l~l:2:2) to afford 2-(2-phenoxy-acetylamino)-isonicotinamide as a colorless solid (0.105g, 58.9 % yield).1H NMR (DMSO-ds, 300 MHz) 10.65(1H, s, CONH), 8.45-8.42(2H, m, CONH2), 8.19(1H, s, pyridine-H), 7.67(1H, s, pyridine-H), 7.49(1H, dd, J=1.5&5.1 Hz, pyridine-H), 7.33-7.28(2H, m, aromatic), 6.98- 6.94(3H, m, aromatic), 4.81 (2H, s, OCH2). |
58.9% | With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; | 121 2-(2-phenoxy-acetylamino)-isonicotinamide To solution of (phenoxy-acetic acid (100 mg, 0.65 mmol), 2-amino isonicotinamide (180 mg, 1.31 mmol) and DMAP (160 mg, 1.31 mmol) in DMF 5 ml was added PyBOP (684 mg, 1.31 mmol), and stirred room temperature. Reaction mixture was poured onto ice cold water, diluted by methanol/MC mixture (10%). The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by PLC (EtOAc:n-Hexanes:MeOH=1:2:1-1:2:2) to afford 242-phenoxy-acetylamino)-isonicotinamide as a colorless solid (0.105 g, 58.9% yield). 1H NMR (DMSO-d6, 300 MHz) 10.65 (1H, s, CONH), 8.45-8.42 (2H, m, CONH2), 8.19 (1H, s, pyridine-H), 7.67 (1H, s, pyridine-H), 7.49 (1H, dd, J=1.5&5.1 Hz, pyridine-H), 7.33-7.28 (2H, m, aromatic), 6.98-6.94 (3H, m, aromatic), 4.81 (2H, s, OCH2). |
With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Example 10 Reduction of 2-Aminoisonicotinamide The procedure at Example 9 was used to prepare 2-amino-4-pyridylcarbinol in 93percent yield by gas chromatographic analysis of the neutralized catholyte. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; | To solution of <strong>[52804-26-9](4-adamantan-1-yl-phenoxy)acetic acid</strong> (70 mg, 0.24 mmol), 2-amino nicotinamide (50.28 mg, 0.36 mmol) and DMAP (59.77 mg, 0.48 mmol) in DMF 5 ml was added PyBOP (452 mg, 0.86 mmol), and stirred room temperature. Reaction mixture was poured onto ice cold water, diluted by methanol/MC mixture (10%). The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by PLC (EtoAC:Hexane:MeOH=3:6:1-2:4:1) to afford 2-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-isonicotinamide as a colorless solid (0.05 g, 50% yield). 1H NMR (DMSO-d6, 300 MHz) 10.62 (1H, s, CONH), 8.43 (2H, m, CONH2), 8.19 (1H, s, pyridine), 7.67 (1H, s, pyridine), 7.49 (1H, d, J=5.1 Hz, pyridine), 7.26 (2H, d, J=9.3, aromatic), 6.89 (2H, d, J=8.4 Hz, aromatic), 4.78 (2H, s, OCH2), 2.03 (3H, brs, adamantyl), 1.82 (6H, s, adamantyl), 1.71 (6H, s, adamantyl). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.3% | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide | 94 2-[2-(4-tert-butyl-phenoxy)-acetylamino]-isonicotinic Acid Methyl Ester A solution of (4-tert-butyl-phenoxy)acetic acid (200.1 mg, 0.96 mmol), 2-amino-isonicotinamide (109.5 mg, 0.72 mmol), DIPEA (0.17 ml, 0.96 mmol) and PyBOP (499.5 mg, 0.96 mmol) in DMF 6.0 mL was stirred, then partitioned between ethyl acetate and water. The organic phase was purified by preparative TLC(Hexane:EtoAC:MeOH=15:3:1) to give 2-[2-(4-tert-butyl-phenoxy)-acetylamino]-isonicotinic acid methyl ester as a white solid (124.0 mg, 50.3% yield). 1H-NMR (CDCl3, 300 Hz) 9.20 (1H, s, NH), 8.83 (1H, s, aromatic-H), 8.45 (1H, d, J=5.1 Hz, aromatic-H), 7.66-7.68 (1H, m, aromatic-H), 7.33-7.37 (2H, m, aromatic-E), 6.93-6.97 (2H, m, aromatic-H), 4.64 (2H, s, CH2), 3.97 (3H, s, CH3), 1.31 (9H, s, CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66.8% | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide | 120 2-(2-p-tolyloxy-acetylamino)isonicotinamide A solution of 4 p-tolyloxy-acetic acid (60.1 mg, 0.36 mmol), 2-amino-isonicotinamide (74.1 mg, 0.54 mmol), DIPEA (0.12 ml, 0.72 mmol) and PyBOP (374.4 mg, 0.72 mmol) in DMF 5.0 mL was stirred, then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by Prep-TLC(CH2Cl2:MeOH=10:1) to give 2-(2-p-tolyloxy-acetylamino)-isonicotinamide as a white solid (68.5 mg, 66.8% yield). 1H-NMR (DMSO-d6, 300 Hz) 10.61 (1H, s, NH), 8.42-8.45 (2H, m, aromatic-H), 8.20 (1H, s, NH2), 7.68 (1H, s, NH2), 7.49-7.51 (1H, m, aromatic-H), 7.10 (2H, d, J=8.7 Hz, aromatic-H), 6.85-6.88 (2H, m, aromatic-H), 4.76 (2H, s, CH2), 2.23 (3H, s, CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; | To solution of (4-fluoro-phenoxy)-acetic acid (100 mg, 0.43 mmol), 2-amino nicotinamide (89.39 mg, 0.65 mmol) and DMAP (106 mg, 0.86 mmol) in DMF 5 ml was added PyBOP (452 mg, 0.86 mmol), and stirred room temperature. Reaction mixture was poured onto ice cold water, diluted by methanol/MC mixture (10%). The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by PLC (EtoAC:Hexaane:MeOH=3:6:1-2:4:1) to afford 2-[2-(4-fluoro-phenoxy)-acetylamino]-isonicotinamide as a colorless solid (0.08 g, 59% yield). 1H NMR (DMSO-d6, 300 MHz) 10.67 (1H, s, CONH), 8.44 (1H, d, J=5.1 Hz, CONH2), 8.41 (1H, s, CONH2), 8.20 (1H, brs, pyridine), 7.68 (1H, brs, pyridine), 7.49 (1H, d, J=1.5 &5.1 Hz: pyridine), 7.16-7.11 (2H, m, aromatic), 7.01-6.97 (2H, m, aromatic), 4.80 (2H, s, OCH2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide 2: pyridine; lithium iodide / 125 °C |