1,2-Dichloroethane → Tert-butyl (2-{13-cyclohexyl-10-[({[(2,2-dimethoxyethyl)(methyl)amino]sulfonyl}amino)carbonyl]-3-methoxy-6,7-dihydro-5H-indolo[2,1-a][2]benzazepin-6-yl}ethyl)methylcarbamate

HRID 1669435Notes

Reaction equation

HRID 1669435 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:40])[CH2:9][CH2:10][CH:11]1[CH2:17][C:16]2[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:15]=2[C:14]2=[C:24]([CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)[C:25]3[CH:26]=[CH:27][C:28]([C:31](O)=[O:32])=[CH:29][C:30]=3[N:13]2[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:41][O:42][CH:43]([O:51][CH3:52])[CH2:44][N:45]([CH3:50])[S:46]([NH2:49])(=[O:48])=[O:47].C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH:34]1([C:24]2[C:25]3[CH:26]=[CH:27][C:28]([C:31]([NH:49][S:46]([N:45]([CH2:44][CH:43]([O:42][CH3:41])[O:51][CH3:52])[CH3:50])(=[O:48])=[O:47])=[O:32])=[CH:29][C:30]=3[N:13]3[CH2:12][CH:11]([CH2:10][CH2:9][N:8]([CH3:40])[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:17][C:16]4[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:15]=4[C:14]=23)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 673450216-{2-[(tert-butoxycarbonyl)(methyl)amino]ethyl}-13-cyclohexyl-3-methoxy-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylic acidHCID 86627889N-(2,2-dimethoxyethyl)-N-methylsulfamide

Product 1

HCID 67342477Tert-butyl (2-{13-cyclohexyl-10-[({[(2,2-dimethoxyethyl)(methyl)amino]sulfonyl}amino)carbonyl]-3-methoxy-6,7-dihydro-5H-indolo[2,1-a][2]benzazepin-6-yl}ethyl)methylcarbamate

Reagents, catalysts & solvents 3

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

Conditions

Temperature
40 °C

Procedure

To a solution of 6-{2-[(tert-butoxycarbonyl)(methyl)amino]ethyl}-13-cyclohexyl-3-methoxy-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid in DCM (0.07M), N-(2,2-dimethoxyethyl)-N-methylsulfamide (2 eq, Example 1, Step 1), EDC (3 eq) and DMAP (5 eq) were added. The mixture was stirred at 40° C. for 3 h, then diluted with EtOAc and washed with 1N HCl, 1N NaOH solution and brine. The organic phase was dried over Na2SO4 and evaporated in vacuo and the residual material was used in the next step without purification. (ES+) m/z 727 (M+H)+.

Workup

  1. washwashed with 1N HCl, 1N NaOH solution and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated in vacuo
  4. customthe residual material was used in the next step without purification

Sources & evidence

ORD record
ord-4d6c85750a014324b48f4aa8c3d21414
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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