4-Methylmorpholine → (2-{2-[2-(2-{2[5-(4-Chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylcarbamoyl]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethyl)-carbamic acid tert-butyl ester

HRID 1689570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689570
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][C:23]([OH:25])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[Cl:54][C:55]1[CH:60]=[CH:59][C:58]([C:61]2[S:65][C:64]([NH2:66])=[N:63][C:62]=2[CH3:67])=[CH:57][C:56]=1[S:68]([CH3:71])(=[O:70])=[O:69]>CN(C)C=O>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][C:23](=[O:25])[NH:66][C:64]1[S:65][C:61]([C:58]2[CH:59]=[CH:60][C:55]([Cl:54])=[C:56]([S:68]([CH3:71])(=[O:70])=[O:69])[CH:57]=2)=[C:62]([CH3:67])[N:63]=1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27560011-(((Tert-butoxy)carbonyl)amino)-3,6,9,12-tetraoxapentadecan-15-oic acidHCID 578311165-[4-Chloro-3-(methylsulfonyl)phenyl]-4-methyl-1,3-thiazol-2-amine

Produkt 1

HCID 86639506(2-{2-[2-(2-{2[5-(4-Chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylcarbamoyl]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethyl)-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-(2-{2-[2-(2-tert-butoxycarbonylamino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propionic acid (690 mg 1.9 mmol), EDAC (403 mg 2.1 mmol), HOBT (284 mg 2.1 mmol), NMM (420 uL 3.8 mmol) and 5-(4-chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylamine (520 mg 1.7 mmol) were combined in dimethylformamide (16 ml) and stirred over night at room temperature. The solvent was removed under reduced pressure and the residue dissolved in dichloromethane (150 ml), washed with 1M HCl aqueous solution (50 ml) and saturated aqueous sodium hydrogen carbonate (50 ml), dried (Magnesium sulphate), filtered and evaporated. The residue was purified by flash chromatography using 50 g IST silica flash cartridge eluting with 0-2% methanol/dichloromethane to yield (2-{2-[2-(2-{2[5-(4-chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylcarbamoyl]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethyl)-carbamic acid tert-butyl ester as an oil (1.1 g residual solvent present) 1H NMR (400 MHz CDCl3) 10.3 (br s, 1H), 8.2 (s, 1H), 7.6 (m, 2H), 7.2 (br s, 1H), 3.9 (t, 2H) 3.8-3.5 (br m, 14H), 3.3 (br m, 5H), 2.8 (t, 2H), 2.4 (s, 3H), 1.4 (s, 9H).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in dichloromethane (150 ml)
  3. washwashed with 1M HCl aqueous solution (50 ml) and saturated aqueous sodium hydrogen carbonate (50 ml)
  4. dry with materialdried (Magnesium sulphate)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 0-2% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-7f97a4e80b7d45339cf9a56dc7b69b8c
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153389B2

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