Tert-butyl-3-chloro-14-cyclohexyl-6-[2-(dimethylamino)ethyl]-7-oxo-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate → 3-Chloro-14-cyclohexyl-6-[2-(dimethylamino)ethyl]-7-oxo-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylic acid

HRID 1714009Notes

Reaction equation

HRID 1714009 reaction equation
C([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]2[C:12]([CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[C:13]3[C:20]4[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=4[CH2:18][N:17]([CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[C:16](=[O:31])[CH2:15][N:14]3[C:32]=2[CH:33]=1)=[O:7])(C)(C)C>C(O)(C(F)(F)F)=O.O.[SiH](CC)(CC)CC>[Cl:25][C:23]1[CH:22]=[CH:21][C:20]2[C:13]3=[C:12]([CH:34]4[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]4)[C:11]4[CH:10]=[CH:9][C:8]([C:6]([OH:7])=[O:5])=[CH:33][C:32]=4[N:14]3[CH2:15][C:16](=[O:31])[N:17]([CH2:26][CH2:27][N:28]([CH3:29])[CH3:30])[CH2:18][C:19]=2[CH:24]=1

Participants

3

Reactant 1

HCID 68509559Tert-butyl-3-chloro-14-cyclohexyl-6-[2-(dimethylamino)ethyl]-7-oxo-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate

Product 1

HCID 668331323-Chloro-14-cyclohexyl-6-[2-(dimethylamino)ethyl]-7-oxo-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylic acid

Reagents, catalysts & solvents 1

HCID 131728328TFA H2O Et3SiHSolvent

Procedure

A solution of tert-butyl-3-chloro-14-cyclohexyl-6-[2-(dimethylamino)ethyl]-7-oxo-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate (from Step 9, 1 eq) in a mixture of TFA:H2O:Et3SiH (95:3:2) (0.03 M) was stirred at RT for 1 h. Volatiles were removed in vacuo and the residue purified by RP-HPLC to afford the title compound; MS (ES+) m/z 494 (M+H)+.

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residue purified by RP-HPLC

Sources & evidence

ORD record
ord-4b6950af21ea45e897e5ee669afa3935
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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