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N-Isopropyl-2-[3-methyl-2,4-dioxo-5-phenyl-3-(3-phenyl-allyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-phenyl acetamide → N-Isopropyl-2-[3-methyl-2,4-dioxo-5-phenyl-3-(3-phenyl-propyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-phenyl acetamide

HRID 343198
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HRID 343198 반응식
[CH:1]([N:4]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:5](=[O:36])[CH2:6][N:7]1[C:13](=[O:14])[C:12]([CH3:24])([CH2:15][CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:11](=[O:25])[N:10]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:9]2[CH:32]=[CH:33][CH:34]=[CH:35][C:8]1=2)([CH3:3])[CH3:2]>C(O)C.[Pd]>[CH:1]([N:4]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:5](=[O:36])[CH2:6][N:7]1[C:13](=[O:14])[C:12]([CH3:24])([CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:11](=[O:25])[N:10]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:9]2[CH:32]=[CH:33][CH:34]=[CH:35][C:8]1=2)([CH3:3])[CH3:2]
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참가 물질

4

반응물 1

HCID 67699497N-Isopropyl-2-[3-methyl-2,4-dioxo-5-phenyl-3-(3-phenyl-allyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-phenyl acetamide

생성물 1

HCID 67700209N-Isopropyl-2-[3-methyl-2,4-dioxo-5-phenyl-3-(3-phenyl-propyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-phenyl acetamide수율 0.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

To a stirring solution of 40 mg (71.7 mmol) of N-Isopropyl-2-[3-methyl-2,4-dioxo-5-phenyl-3-(3-phenyl-allyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-phenyl acetamide, prepared as in Example 11, in 3 mL absolute ethanol is added 10 mg of 10% palladium on carbon. The reaction vessel is placed on a Parr hydrogenation apparatus, evacuated, and then pressurized with H2 gas to 40 psi and shaken for 2 h at RT. The reaction mixture is filtered through Celite to remove the catalyst and the solvent removed in vacuo. Purification of the resulting material via reverse phase MPLC using a C-18 column and 70% acetonitrile/30% H2O with 0.1% TFA as eluent followed by lyophilization afforded 29 mg of the title compound as a white amorphous solid: 1H NMR (CDCl3, 300 MHz) δ7.49-6.96 (m, 19H), 6.72 (d, 1H, J=8.0), 5.09 (m, 1H), 4.38 (d, 1H, J=16.3), 3.92 (d, 1H, J=16.3), 2.28 (m, 2H), 1.67-1.50 (m, 6H), 1.34 (m, 1H), 1.12 (m, 6H); low resolution MS (FAB)m/e 560 (MH+), 425, 397, 223.

후처리

  1. customevacuated
  2. filtrationThe reaction mixture is filtered through Celite
  3. customto remove the catalyst
  4. customthe solvent removed in vacuo
  5. customPurification of the resulting material via reverse phase MPLC

출처 및 근거

ORD 기록
ord-8c188b648f8544de911b56e276320d89
출처 데이터셋
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05859007

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