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Dimethylformamide → (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]piperazine

HRID 10169
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HRID 10169 반응식
[CH2:1]1[O:10][C:4]([CH2:6][CH2:7][CH2:8]Cl)([CH3:5])[O:3][CH2:2]1.[F:11][C:12]([F:42])([F:41])[C:13]1[CH:14]=[C:15]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[C:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][C@H:19]1[CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)=[O:17].C(N(C(C)C)CC)(C)C.CN(C)C=O>O>[F:40][C:37]([F:38])([F:39])[C:35]1[CH:34]=[C:15]([CH:14]=[C:13]([C:12]([F:11])([F:41])[F:42])[CH:36]=1)[C:16]([N:18]1[CH2:23][CH2:22][N:21]([CH2:8][CH2:7][CH2:6][C:4]2([CH3:5])[O:10][CH2:1][CH2:2][O:3]2)[CH2:20][C@H:19]1[CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)=[O:17]
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참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 800792-(3-Chloropropyl)-2-methyl-1,3-dioxolaneHCID 81531DiisopropylethylamineHCID 10972505(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine

생성물 1

HCID 58681859(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]piperazine수율 40%

시약·촉매·용매 1

HCID 962Water용매

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온도
90 °C

실험 절차

A mixture of 5-chloro-2-pentanone ethylene ketal (0.54 g), (2R)-1-[3,5-bis(trifluoro-methyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine (1.37 g), diisopropylethylamine (0.6 mL), and dimethylformamide (25 mL) was heated overnight, at 90°C. After cooling to room temperature the mixture was poured in water and extracted with ethyl acetate. The organic layer was dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH 95/15) to afford (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]piperazine (0.7 g, 40%). MH+ 584.

후처리

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH 95/15)

출처 및 근거

ORD 기록
ord-01898ff63c1d4a31a48358210ecd48cd
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07094779B2

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