1,2-Dichloroethane → 7-({2-[benzyl(methyl)amino]ethoxy}methyl)-14-cyclohexyl-N-{[(2,2-dimethoxyethyl)(methyl)amino]sulfonyl}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxamide

HRID 1669494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669494
[CH2:1]([N:8]([CH3:41])[CH2:9][CH2:10][O:11][CH2:12][CH:13]1[CH2:20][N:19]2[C:21]3[CH:22]=[C:23]([C:34]([OH:36])=O)[CH:24]=[CH:25][C:26]=3[C:27]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[C:18]2[C:17]2[CH:37]=[CH:38][CH:39]=[CH:40][C:16]=2[O:15][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.[CH3:46][O:47][CH:48]([O:56][CH3:57])[CH2:49][N:50]([CH3:55])[S:51]([NH2:54])(=[O:53])=[O:52]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH2:1]([N:8]([CH3:41])[CH2:9][CH2:10][O:11][CH2:12][CH:13]1[CH2:20][N:19]2[C:21]3[CH:22]=[C:23]([C:34]([NH:54][S:51]([N:50]([CH2:49][CH:48]([O:47][CH3:46])[O:56][CH3:57])[CH3:55])(=[O:53])=[O:52])=[O:36])[CH:24]=[CH:25][C:26]=3[C:27]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[C:18]2[C:17]2[CH:37]=[CH:38][CH:39]=[CH:40][C:16]=2[O:15][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 111,2-DichloroethaneHCID 86627889N-(2,2-dimethoxyethyl)-N-methylsulfamideHCID 866279097-({2-[benzyl(methyl)amino]ethoxy}methyl)-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid

Produkt 1

HCID 866279107-({2-[benzyl(methyl)amino]ethoxy}methyl)-14-cyclohexyl-N-{[(2,2-dimethoxyethyl)(methyl)amino]sulfonyl}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A solution of (7R or 7S)-7-({2-[benzyl(methyl)amino]ethoxy}methyl)-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid in dry DCM (0.06 M) was treated with DMAP (3 eq), EDC (1.5 eq) and N-(2,2-dimethoxyethyl)-N-methylsulfamide (prepared as described in example 1 step 1). The mixture was stirred at 40° C. for 2 h, and then diluted with EtOAc, washed with 1N HCl (aq), sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound. The crude material was used in the next step without further purification. (ES+) m/z 733 (M+H)+.

Aufarbeitung

  1. washwashed with 1N HCl (aq), sat. aq. NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-87069685ba9d403287d7e5f4fd467924
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989438B2

Notizen zur Reaktion

Wird geladen…