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[ CAS No. 13538-42-6 ] {[proInfo.proName]}

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Chemical Structure| 13538-42-6
Chemical Structure| 13538-42-6
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Product Details of [ 13538-42-6 ]

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 :

Safety of [ 13538-42-6 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P301+P310 UN#:2811
Hazard Statements:H301 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 13538-42-6 ]

* 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 [ 13538-42-6 ]

[ 13538-42-6 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 6937-03-7 ]
  • [ 13538-42-6 ]
YieldReaction ConditionsOperation 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 %].

  • 2
  • [ 1878-91-7 ]
  • [ 13538-42-6 ]
  • 2-[2-(4-bromo-phenoxy)-acetylamino]-isonicotinamide [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 3
  • [ 13538-42-6 ]
  • [ 1798-04-5 ]
  • 2-[2-(4-tert-butyl-phenoxy)-acetylamino]-isonicotinamide [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 4
  • [ 13538-42-6 ]
  • [ 1798-04-5 ]
  • 2-(2-p-tolyloxy-acetylamino)-isonicotinamide [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 5
  • [ 13538-42-6 ]
  • [ 122-59-8 ]
  • 2-(2-phenoxy-acetylamino)-isonicotinamide [ No CAS ]
YieldReaction ConditionsOperation 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
YieldReaction ConditionsOperation 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.
  • 8
  • [ 13538-42-6 ]
  • [ 52804-26-9 ]
  • 2-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-isonicotinamide [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 9
  • [ 13538-42-6 ]
  • [ 1798-04-5 ]
  • 2-[2-(4-tert-butyl-phenoxy)-acetylamino]-isonicotinic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 10
  • [ 13538-42-6 ]
  • [ 940-64-7 ]
  • 2-(2-p-tolyloxy-acetylamino)-isonicotinamide [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 11
  • [ 13538-42-6 ]
  • [ 405-79-8 ]
  • 2-[2-(4-fluoro-phenoxy)-acetylamino]-isonicotinamide [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 12
  • [ 13538-42-6 ]
  • [ 1798-04-5 ]
  • 2-[2-(4-tert-butyl-phenoxy)-acetylamino]-isonicotinic acid [ No CAS ]
YieldReaction ConditionsOperation 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
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