2-Amino-3,4-dimethylpyridine → Ethyl 4-benzyl-6-(2-(1-methyl-1H-pyrazole-4-sulfonamido)ethoxy)chroman-3-ylcarbamate

HRID 532134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 532134
[Cl-].[CH2:2]([CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH2:20][CH2:21][NH3+:22])[CH:17]=2)[O:12][CH2:11][CH:10]1[NH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CC1C=CN=C(N)C=1C.[CH3:38][N:39]1[CH:43]=[C:42]([S:44](Cl)(=[O:46])=[O:45])[CH:41]=[N:40]1>C(Cl)Cl>[CH2:2]([CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH2:20][CH2:21][NH:22][S:44]([C:42]3[CH:41]=[N:40][N:39]([CH3:38])[CH:43]=3)(=[O:46])=[O:45])[CH:17]=2)[O:12][CH2:11][CH:10]1[NH:23][C:24](=[O:25])[O:26][CH2:27][CH3:28])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 110078842-Amino-3,4-dimethylpyridineHCID 170247301-methyl-1H-pyrazole-4-sulfonyl chlorideHCID 71245553HCID 71245553, Verbindung

Produkt 1

HCID 71245390Ethyl 4-benzyl-6-(2-(1-methyl-1H-pyrazole-4-sulfonamido)ethoxy)chroman-3-ylcarbamateAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

100 mg (0.25 mmol) of 2-(4-benzyl-3-(ethoxycarbonylamino)chroman-6-yloxy)ethanaminium chloride were dissolved in 5 ml methylene dichloride. Then, 95 mg (0.79 mmol) dimethyl aminopyridine and 54 mg (0.30 mmol) 1-methyl-1H-pyrazole-4-sulfonyl chloride were added. The reaction mixture was stirred at room temperature over night. The mixture was concentrated in vacuo and the residue was dissolved in ethylacetate and water. The phases were separated. The organic phase was washed with saturated ammonium chloride solution (2×), dried over MgSO4 and concentrated (127 mg crude). The crude material was purified by column chromatography to give 118 mg (0.23 mmol, 93%) of the desired product.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethylacetate
  3. customThe phases were separated
  4. washThe organic phase was washed with saturated ammonium chloride solution (2×)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated (127 mg crude)
  7. customThe crude material was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-eaf4f63aaff94bdbb347dbab44552056
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853196B2

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