Diisopropylethylamine → 3-{[(2,3-Diaza-spiro[4.4]non-3-en-2-yl)-ethylamino-methylene]-sulfamoyl}-benzoic acid methyl ester

HRID 1044711

Reaktionsgleichung

Reaktionsgleichung von HRID 1044711
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:5]=1.CCN(C(C)C)C(C)C.[CH2:24]([NH:26][C:27]([N:29]1[N:33]=[CH:32][C:31]2([CH2:37][CH2:36][CH2:35][CH2:34]2)[CH2:30]1)=[NH:28])[CH3:25]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10](=[O:12])(=[O:11])[N:28]=[C:27]([N:29]2[N:33]=[CH:32][C:31]3([CH2:37][CH2:36][CH2:35][CH2:34]3)[CH2:30]2)[NH:26][CH2:24][CH3:25])[CH:5]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 113339Benzoic acid, 3-(chlorosulfonyl)-, methyl esterHCID 178464598HCID 178464598, Verbindung

Produkt 1

HCID 1784646503-{[(2,3-Diaza-spiro[4.4]non-3-en-2-yl)-ethylamino-methylene]-sulfamoyl}-benzoic acid methyl esterAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4.07 g 3-chlorosulfonyl-benzoic acid methyl ester in 150 mL DCM were added 17.69 mL (6.0 equiv.) DiPEA and 4.00 g (1.0 equiv.) N-ethyl-2,3-diaza-spiro[4.4]non-3-ene-2-carboxamidine. The reaction mixture was stirred overnight at room temperature under N2 atmosphere, and extracted with water. The organic phase was dried over Na2SO4 and evaporated, and the residue was purified by automated flash chromatography (EtOAc/PA 1:1) to give 4.80 g (71%) of a yellow solid. 1H NMR (400 MHz, CDCl3) δ 1.16 (t, J=8 Hz, 3H), 1.62-1.86 (m, 8H), 3.42-3.53 (m, 2H), 3.87 (s, 2H), 3.95 (s, 3H), 6.83 (s, 1H), 6.83-6.95 (broad peak, 1H), 7.56 (t, J=8 Hz, 1H), 8.13-8.18 (m, 2H), 8.61 (s, 1H).

Aufarbeitung

  1. extractionextracted with water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated
  4. customthe residue was purified by automated flash chromatography (EtOAc/PA 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-54d396e0d79e4cb5910ed097cc451ebb
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563723B2

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