1,2-Dichloroethane → (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

HRID 1669406Notes

Reaction equation

HRID 1669406 reaction equation
[Cl-].[CH2:2]([NH+:9]([CH3:41])[CH2:10][CH2:11][O:12][C@H:13]1[CH2:20][N:19]2[C:21]3[CH:22]=[C:23]([C:34](O)=[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:37]=[CH:38][CH:39]=[CH:40][C:16]=2[O:15][CH2:14]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=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]>CN(C1C=CN=CC=1)C.C(Cl)Cl.CCOC(C)=O>[CH2:2]([N:9]([CH3:41])[CH2:10][CH2:11][O:12][C@H: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: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:37]=[CH:38][CH:39]=[CH:40][C:16]=2[O:15][CH2:14]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 86627889N-(2,2-dimethoxyethyl)-N-methylsulfamideHCID 86627892N-benzyl-2-{[(7S)-11-carboxy-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocin-7-yl]oxy}-N-methylethanaminium chloride

Product 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

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

A solution (0.06 M) of N-benzyl-2-{[(7S)-11-carboxy-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocin-7-yl]oxy}-N-methylethanaminium chloride and DMAP (3 eq) in anhydrous DCM, was treated with 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 14 h, and then diluted with EtOAc, washed with aqueous sat. aq. NaHCO3 and brine. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to give the title compound. The product was used in the next step without further purification. (ES+) m/z 719 (M+H)+.

Workup

  1. washwashed with aqueous sat. aq. NaHCO3 and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9532a56b168542edb8b49d3d8da0a83d
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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