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

HRID 1669495Notes

Reaction equation

HRID 1669495 reaction equation
[CH2:1]([N:8](C)[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:36][S:37]([N:40]([CH2:42][CH:43]([O:46][CH3:47])[O:44][CH3:45])[CH3:41])(=[O:39])=[O:38])=[O:35])[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:48]=[CH:49][CH:50]=[CH:51][C:16]=2[O:15][CH2:14]1)C1C=CC=CC=1.CC(O)=O>CO.[Pd]>[CH:28]1([C:27]2[C:26]3[CH:25]=[CH:24][C:23]([C:34]([NH:36][S:37]([N:40]([CH2:42][CH:43]([O:46][CH3:47])[O:44][CH3:45])[CH3:41])(=[O:39])=[O:38])=[O:35])=[CH:22][C:21]=3[N:19]3[C:18]=2[C:17]2[CH:48]=[CH:49][CH:50]=[CH:51][C:16]=2[O:15][CH2:14][CH:13]([CH2:12][O:11][CH2:10][CH2:9][NH:8][CH3:1])[CH2:20]3)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 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

Product 1

HCID 8662791114-cyclohexyl-N-{[(2,2-dimethoxyethyl)(methyl)amino]sulfonyl}-7-{[2-(methylamino)ethoxy]methyl}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (7R or 7S)-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 in MeOH (0.06 M) was treated with AcOH (1 eq) and Pd/C (2 eq). The resulting mixture was stirred for 12 h under an H2 atmosphere. The mixture was filtered and then concentrated in vacuo to afford the title compound. The crude material was used in the next step without further purification. (ES+) m/z 643 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57a8c81f770d48128b7f7d9b40faddaf
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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