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

HRID 1669407Notes

Reaction equation

HRID 1669407 reaction equation
[CH2:1]([N:8](C)[CH2:9][CH2:10][O:11][C@H:12]1[CH2:19][N:18]2[C:20]3[CH:21]=[C:22]([C:33]([NH:35][S:36]([N:39]([CH2:41][CH:42]([O:45][CH3:46])[O:43][CH3:44])[CH3:40])(=[O:38])=[O:37])=[O:34])[CH:23]=[CH:24][C:25]=3[C:26]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[C:17]2[C:16]2[CH:47]=[CH:48][CH:49]=[CH:50][C:15]=2[O:14][CH2:13]1)C1C=CC=CC=1>CO.[Pd]>[CH:27]1([C:26]2[C:25]3[CH:24]=[CH:23][C:22]([C:33]([NH:35][S:36]([N:39]([CH2:41][CH:42]([O:45][CH3:46])[O:43][CH3:44])[CH3:40])(=[O:38])=[O:37])=[O:34])=[CH:21][C:20]=3[N:18]3[C:17]=2[C:16]2[CH:47]=[CH:48][CH:49]=[CH:50][C:15]=2[O:14][CH2:13][C@@H:12]([O:11][CH2:10][CH2:9][NH:8][CH3:1])[CH2:19]3)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

4

Reactant 1

HCID 67344821(7S)-7-{2-[benzyl(methyl)amino]ethoxy}-14-cyclohexyl-N-{[(2,2-dimethoxyethyl)(methyl)amino]sulfonyl}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxamide

Product 1

HCID 67345577(7S)-14-cyclohexyl-N-{[(2,2-dimethoxyethyl)(methyl)amino]sulfonyl}-7-[2-(methylamino)ethoxy]-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C (1 eq) was added to a solution of (7S)-7-{2-[benzyl(methyl)amino]ethoxy}-14-cyclohexyl-N-{[(2,2-dimethoxyethyl)(methyl)amino]sulfonyl}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxamide (0.06 M) in MeOH. The resulting mixture was stirred for 12 h under H2 atmosphere. The mixture was filtered and then concentrated in vacuo to afford the title compound. The product was used in the next step without further purification. (ES+) m/z 629 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b6ace4c92ee54e61a91e9ccb64398643
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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