Triethylamine → HCID 68683130, Verbindung

HRID 1442675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1442675
[CH3:1][O:2][C:3](=[O:18])[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[N:17]=[CH:16][CH:15]=[N:14]2)=[CH:9][CH:8]=1.CCN(CC)CC.[CH:26]1([CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=2)[CH2:28][CH2:27]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:18])[CH2:4][N:5]([S:37]([C:34]1[CH:33]=[CH:32][C:31]([O:30][CH2:29][CH:26]2[CH2:27][CH2:28]2)=[CH:36][CH:35]=1)(=[O:39])=[O:38])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[N:14]=[CH:15][CH:16]=[N:17]2)=[CH:11][CH:12]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 113686084-(cyclopropylmethoxy)benzenesulfonyl ChlorideHCID 68685133HCID 68685133, Verbindung

Produkt 1

HCID 68683130HCID 68683130, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

To a solution of 79.5 g (323.2 mmol) of the compound of stage 3.2, 80.9 ml (581.6 mmol) of Et3N and 1.97 g (16.1 mmol) of DMAP in 1000 ml of CH2Cl2, a solution of 99.6 g (404 mmol ) of 4-cyclopropylmethoxy-benzenesulfonyl chloride in 150 ml of CH2Cl2 is added and stirred for 60 min. at 0-5° C. After stirring for additional 18 h at r.t., the reaction mixture is quenched with ice water and extracted with CH2Cl2. The combined extracts are washed with H2O, brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by CC on silica gel (n-Hexane:AcOEt=4:1-2:1) to give the title compound as colorless solid; 1H-NMR (400 MHz, CDCl3): 0.35-0.45 (m, 2H), 0.65-0.75 (m, 2H), 1.25-1.35 (m, 1H), 3.58 (s, 3H), 3.87 (d, 2H, J=7.04 Hz), 3.94 (s, 2H), 4.52 (s, 2H), 6.99 (d, 2H, J=7.04 Hz), 7.37 (d, 2H, J=8.56 Hz), 7.81(s, 2H), 7.82 (d, 2H, J=7.04 Hz), 8.02 (d, 2H, J=8.56 Hz).

Aufarbeitung

  1. stirringAfter stirring for additional 18 h at r.t.
  2. customthe reaction mixture is quenched with ice water
  3. extractionextracted with CH2Cl2
  4. washThe combined extracts are washed with H2O, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by CC on silica gel (n-Hexane:AcOEt=4:1-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-f653a314837c47d39beac0afba698944
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659293B2

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