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Chemical Structure| 558441-90-0 Chemical Structure| 558441-90-0

Structure of 558441-90-0

Chemical Structure| 558441-90-0

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Product Details of [ 558441-90-0 ]

CAS No. :558441-90-0
Formula : C21H27N5
M.W : 349.47
SMILES Code : NCCCCN(CC1=NC2=CC=CC=C2N1)C3CCCC4=C3N=CC=C4

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Application In Synthesis of [ 558441-90-0 ]

* 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 [ 558441-90-0 ]

[ 558441-90-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 558441-90-0 ]
  • [ 79-37-8 ]
  • [ 13958-93-5 ]
  • N-{4-[(1H-benzimidazol-2-ylmethyl)-(R)-5,6,7,8-tetrahydro-quinolin-8-yl-amino]-butyl}-3,5-dichloro-isonicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; Example 155 Compound 155: Preparation of N-{4-[(1H-benzimidazol-2-ylmethyl)-(R)-5,6,7,8-tetrahydroquinolin-8-yl-amino]-butyl}-3,5-dichloro-isonicotinamide. To a suspension of <strong>[13958-93-5]3,5-dichloropyridine-4-carboxylic acid</strong> (135 mg, 0.70 mmol) and DMF (2 drops) in CH2Cl2 (7 mL) was added oxalyl chloride (0.18 mL, 2.1 mmol). The resulting suspension was stirred at room temperature under nitrogen for 35 minutes and then the solvent was evaporated under reduced pressure. The crude acid chloride was dried under reduced pressure, and then a solution of N1-(1H-Benzimidazol-2-ylmethyl)-N1-(R)-5,6,7,8-tetrahydroquinolin-8-yl-butane-1,4-diamine (120 mg, 0.344 mmol) in THF (4 mL) and NEt3 (0.06 mL, 0.4 mmol) were added. The resulting suspension was stirred at room temperature under nitrogen for 1 hour. The reaction was diluted with saturated aqueous NaHCO3 (25 mL) and was extracted with CH2Cl2 (25 mL*3). The combined organic solution was dried (MgSO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (CH2Cl2/MeOH/NH4OH, 32:1:0.2) gave the amide as a white foam (134 mg, 0.256 mmol, 74%). 1H NMR (CDCl3) delta 1.47-1.61 (m, 4H), 1.63-1.78 (m, 1H), 1.81-195 (m, 1H), 2.02-2.13 (m, 1H), 2.15-2.25 (m, 1H), 2.60-2.85 (m, 4H), 3.10-3.23 (m, 1H), 3.31-3.43 (m, 1H), 3.87 (d, 1H, J=16.2 Hz), 3.98 (d, 1H, J=16.2 Hz), 4.05 (dd, 1H, J=9.6, 5.7 Hz), 6.94 (br. t, 1H), 7.12 (dd, 1H, J=7.8, 4.8 Hz), 7.15-7.20 (m, 2H), 7.42 (d, 1H, J=7.8 Hz), 7.44-7.62 (m, 2H), 8.39 (s, 2H), 8.47 (d, 1H, J=4.8 Hz). 13C NMR (CDCl3) delta 21.6, 23.9, 25.8, 26.9, 29.4, 39.6, 49.6, 50.5, 62.1, 122.1, 122.7, 129.2, 135.1, 138.0, 143.2, 146.8, 147.7, 156.4, 157.7, 162.6. ES-MS m/z 523 (M+H), 525 (M+2+H). Anal. Calcd. for C27H28Cl2N6O.0.3H2O.0.2CH2Cl2: C, 59.85; H, 5.35; N, 15.40; Cl, 15.59. Found: C, 59.62; H, 5.38; N, 15.22; Cl, 15.98.
 

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