Dimethyl Sulfoxide → Methyl 13-cyclohexyl-6-formyl-5-methyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-10-carboxylate

HRID 1669424Notes

Reaction equation

HRID 1669424 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH:11]1([C:17]2[C:18]3[CH:19]=[CH:20][C:21]([C:40]([O:42][CH3:43])=[O:41])=[CH:22][C:23]=3[N:24]3[C:30]=2[C:29]2[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=2[N:27]([CH3:35])[CH:26]([C:36](OC)=[O:37])[CH2:25]3)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.CCN(CC)CC>C(Cl)Cl>[CH:11]1([C:17]2[C:18]3[CH:19]=[CH:20][C:21]([C:40]([O:42][CH3:43])=[O:41])=[CH:22][C:23]=3[N:24]3[C:30]=2[C:29]2[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=2[N:27]([CH3:35])[CH:26]([CH:36]=[O:37])[CH2:25]3)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 66674609Dimethyl 13-cyclohexyl-5-methyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-6,10-dicarboxylate

Product 1

HCID 86627899Methyl 13-cyclohexyl-6-formyl-5-methyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-10-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
-78 °C

Procedure

DMSO (5 eq) was dissolved in DCM and the solution was cooled to −78° C. At this temperature a 2M solution of oxalylchloride in DCM (2.5 eq) was added slowly and the mixture was stirred for 25 min at −78° C. A solution of dimethyl 13-cyclohexyl-5-methyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-6,10-dicarboxylate (1 eq) in DCM (0.09M) was added slowly at −78° C. and stirring was continued for 25 min at this temperature. Then NEt3 (8 eq) was added and the resulting slurry was placed into an ice bath at 0° C. The mixture was left stirring for 90 min, then diluted with DCM and extracted with sat. aq. NH4Cl, sat. aq. NaHCO3 and brine. After drying over Na2SO4 all volatiles were evaporated in vacuo. The product was obtained as a deep-yellow solid, which was filtered with DCM over a pad of silica. After evaporation of the solvent the product was obtained as a yellowish solid (quant.). (ES+) m/z 417 (M+H)+.

Workup

  1. stirringstirring
  2. waitwas continued for 25 min at this temperature
  3. customthe resulting slurry was placed into an ice bath at 0° C
  4. waitThe mixture was left
  5. stirringstirring for 90 min
  6. extractionextracted with sat. aq. NH4Cl, sat. aq. NaHCO3 and brine
  7. dry with materialAfter drying over Na2SO4 all volatiles
  8. customwere evaporated in vacuo
  9. customThe product was obtained as a deep-yellow solid, which
  10. filtrationwas filtered with DCM over a pad of silica
  11. customAfter evaporation of the solvent the product
  12. customwas obtained as a yellowish solid (quant.)

Sources & evidence

ORD record
ord-82d9565a27834bffaaef68013afe63de
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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