Triethylamine → HCID 11233557, 화합물

HRID 1991209

반응식

HRID 1991209 반응식
[F:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[F:11].C(N(CC)CC)C.Br[CH2:20][C:21]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1)=[O:22]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:11][C:3]1[CH:4]=[CH:5][C:6]2[N:7]=[CH:8][N:9]([CH2:20][C:21]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[CH:25]=3)=[O:22])[C:10]=2[C:2]=1[F:1]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 23171522-bromo-N-[3-(trifluoromethyl)phenyl]acetamideHCID 27369164,5-Difluorobenzimidazole

생성물 1

HCID 11233557HCID 11233557, 화합물수율 25%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of 4,5-difluoro-1H-benzimidazole (20 mg, 0.13 mmol) in toluene (260 μL), triethylamine (18 μL, 0.13 mmol) and 2-bromo-N-[3-(trifluoromethyl)phenyl]acetamide (37 mg, 0.13 mmol) were added. The reaction mixture was microwave-irradiated in a sealed vial at 120° C. for 30 min. The vial was cooled, opened and the contents dissolved in 20 mL ethyl acetate. The solution was washed with water (5 mL), saturated aqueous NaHCO3 (5 mL) and brine (5 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. Separation of the isomers in the crude product was performed on flash silica column using neat ethyl acetate to yield the title compound (11.3 mg, 25%). MS (ESI) m/z: 355.8 [M+H] 1H NMR (400 MHz, MeOD) δ ppm 5.31 (s, 2H), 7.20 (ddd, J=11.4, 9.0, 7.5 Hz, 1H), 7.40 (d, J=7.8 Hz, 1H), 7.47 (ddd, J=8.9, 3.7, 1.3 Hz, 1H), 7.52 (t, J=8.1 Hz, 1H), 7.79 (d, J=8.8 Hz, 1H), 7.96 (s, 1H), 8.20 (s, 1H).

후처리

  1. additionwere added
  2. customThe reaction mixture was microwave-irradiated in a sealed vial at 120° C. for 30 min
  3. temperatureThe vial was cooled
  4. washThe solution was washed with water (5 mL), saturated aqueous NaHCO3 (5 mL) and brine (5 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customSeparation of the isomers in the crude product

출처 및 근거

ORD 기록
ord-09f8c0b82a214a57862cb7729af5df37
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645784B2

연결된 노트

불러오는 중…