Dimethyl Sulfoxide → Methyl 13-cyclohexyl-6-formyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

HRID 421966노트

반응식

HRID 421966 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:37]([O:39][CH3:40])=[O:38])=[CH:22][C:23]=3[N:24]3[CH2:30][CH:29]([CH2:31][OH:32])[CH2:28][C:27]4[CH:33]=[CH:34][CH:35]=[CH:36][C:26]=4[C:25]=23)[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:37]([O:39][CH3:40])=[O:38])=[CH:22][C:23]=3[N:24]3[CH2:30][CH:29]([CH:31]=[O:32])[CH2:28][C:27]4[CH:33]=[CH:34][CH:35]=[CH:36][C:26]=4[C:25]=23)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 16072734methyl 13-cyclohexyl-6-(hydroxymethyl)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

생성물 1

HCID 86640311Methyl 13-cyclohexyl-6-formyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-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 left stirring for 25 min at −78° C. A solution of methyl 13-cyclohexyl-6-(hydroxymethyl)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate (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 stirred for 90 min, then diluted with DCM and extracted with water, HCl 1N, sat. aq. NaHCO3 and brine. After drying over Na2SO4 all volatiles were evaporated in vacuo. After evaporation of the solvent the product was obtained as a yellowish solid (quant.). (ES+) m/z 402 (M+H)+.

후처리

  1. waitthe mixture was left
  2. stirringstirring
  3. waitwas continued for 25 min at this temperature
  4. customthe resulting slurry was placed into an ice bath at 0° C
  5. stirringThe mixture was stirred for 90 min
  6. extractionextracted with water, HCl 1N, sat. aq. NaHCO3 and brine
  7. dry with materialAfter drying over Na2SO4 all volatiles
  8. customwere evaporated in vacuo
  9. customAfter evaporation of the solvent the product
  10. customwas obtained as a yellowish solid (quant.)

출처 및 근거

ORD 기록
ord-5a8b09bda8fb45bba391ba78e43cab5e
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101595B2

반응 노트

불러오는 중…