Dichloromethane → 2-amino-3-{4-[4-(2-carbamoyl-ethyl)-phenoxy]-phenyl}-N,N-dimethyl-propionamide hydrochloride

HRID 748984Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 748984
C(OC(=O)[NH:7][CH:8]([C:28](=[O:32])[N:29]([CH3:31])[CH3:30])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25](=[O:27])[NH2:26])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(C)(C)C.C(Cl)[Cl:35]>>[ClH:35].[NH2:7][CH:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25](=[O:27])[NH2:26])=[CH:21][CH:22]=2)=[CH:12][CH:11]=1)[C:28]([N:29]([CH3:31])[CH3:30])=[O:32]

Komponenten

3

Edukt 2

HCID 6344DichloromethaneHCID 59762815(2-{4-[4-(2-Carbamoylethyl)-phenoxy]-phenyl}-1-dimethylcarbamoylethyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 159824562-amino-3-{4-[4-(2-carbamoyl-ethyl)-phenoxy]-phenyl}-N,N-dimethyl-propionamide hydrochloride

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

The amide compound 11 (1.5 g) was dissolved in CH2Cl2 (30 mL) and cooled to 0-5° C. Hydrogen chloride gas was bubbled through this solution for 20 min. The bubbling was discontinued and the reaction mixture was stirred at room temperature for 1 h. The excess HCl was degassed and the CH2Cl2 was removed. The residual solid was triturated with EtOAc (2×50 mL), decanted, and dried to yield the desired compound 12 as a white amorphous solid that was extremely hygroscopic (1.0 g, 77%). 1H NMR (DMSO-d6): 7.29 (br, 1H), 7.20 (overlapped d, J=8.8 Hz, 2H), 7.19 (overlapped d, J=8.8 Hz, 2H), 6.88 (overlapped d, J=8.4 Hz, 2H), 6.87 (overlapped d, J=8.4 Hz, 2H), 6.87 (overlapped d, J=8.8 Hz, 2H), 6.76 (br, 1H), 4.63 (m, 1H), 2.83 (s, 3H), 2.54-2.78 (m, 7H), 2.34 (t, J=8.4 Hz, 2H).

Aufarbeitung

  1. customHydrogen chloride gas was bubbled through this solution for 20 min
  2. customThe excess HCl was degassed
  3. customthe CH2Cl2 was removed
  4. customThe residual solid was triturated with EtOAc (2×50 mL)
  5. customdecanted
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0c5169e974e244b4b59fea8fc694b805
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399786B2

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