Dimethyl Sulfide → 14-Cyclohexyl-5-methyl-7,8-dihydroimidazo[4,5,1-jk]indolo[1,2-d][1,4]-benzodiazepine-11-carboxylic acid

HRID 1518232Notes

Reaction equation

HRID 1518232 reaction equation
S(C)C.[C:4]([NH:7][C:8]1[C:18]2[NH:17][C:16](=O)[CH2:15][N:14]3[C:20]4[CH:21]=[C:22]([C:33]([O:35]C)=[O:34])[CH:23]=[CH:24][C:25]=4[C:26]([CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)=[C:13]3[C:12]=2[CH:11]=[CH:10][CH:9]=1)(=O)[CH3:5]>C1COCC1>[CH:27]1([C:26]2[C:25]3[CH:24]=[CH:23][C:22]([C:33]([OH:35])=[O:34])=[CH:21][C:20]=3[N:14]3[C:13]=2[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]4[N:7]=[C:4]([CH3:5])[N:17]([C:18]=24)[CH2:16][CH2:15]3)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

4

Reactant 2

HCID 1068Dimethyl Sulfide2×HCID 68705017methyl 4-(acetylamino)-13-cyclohexyl-6-oxo-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-10-carboxylate

Product 1

HCID 5914281614-Cyclohexyl-5-methyl-7,8-dihydroimidazo[4,5,1-jk]indolo[1,2-d][1,4]-benzodiazepine-11-carboxylic acidYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Me2S complex (2M in THF) (20 eq) was added to a stirred solution of methyl 4-(acetylamino)-13-cyclohexyl-6-oxo-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-10-carboxylate in anhydrous THF (0.02 M) at RT under N2. After 45 min further BH3.Me2S complex (2M in THF) (5 eq) were introduced and the reaction left to stir for 1 h. The reaction was quenched by cautious addition of 1N HCl (aq) and MeOH before partitioning between saturated NaHCO3 (aq) and EtOAc. The organics were washed with water, brine before being dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the crude product. Purification by flash chromatography (3% MeOH/CH2Cl2) afforded the title compound (36%). MS (ES+) m/z 414 (M+H)+.

Workup

  1. waitthe reaction left
  2. customThe reaction was quenched by cautious addition of 1N HCl (aq) and MeOH
  3. custombefore partitioning between saturated NaHCO3 (aq) and EtOAc
  4. washThe organics were washed with water, brine
  5. dry with materialbefore being dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford the crude product
  9. customPurification by flash chromatography (3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3b1d8e9203894cdeab0a725c667c219d
Source dataset
uspto-grants-2012_07
Patent number
US08232390B2

Reaction notes

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