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

HRID 1669424노트

반응식

HRID 1669424 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매4회

반응 조건

온도
-78 °C

실험 절차

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)+.

후처리

  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.)

출처 및 근거

ORD 기록
ord-82d9565a27834bffaaef68013afe63de
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989438B2

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