Sodium hydride → 2-[2,4-Dioxo-5-phenyl-3-(3-phenyl-allyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-phenyl acetamide

HRID 343110

반응식

HRID 343110 반응식
[O:1]=[C:2]1[N:8]([CH2:9][C:10]([N:12]([CH:19]([CH3:21])[CH3:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])[C:7]2[CH:22]=[CH:23][CH:24]=[CH:25][C:6]=2[N:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:4](=[O:32])[CH2:3]1.[H-].[Na+].[CH2:35](Br)/[CH:36]=[CH:37]/[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>CN(C=O)C>[O:1]=[C:2]1[N:8]([CH2:9][C:10]([N:12]([CH:19]([CH3:21])[CH3:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])[C:7]2[CH:22]=[CH:23][CH:24]=[CH:25][C:6]=2[N:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:4](=[O:32])[CH:3]1[CH2:35][CH:36]=[CH:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 5357478Cinnamyl bromideHCID 108124012-(2,4-Dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl acetamide

생성물 1

HCID 676981572-[2,4-Dioxo-5-phenyl-3-(3-phenyl-allyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-phenyl acetamide수율 83.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirring solution of 250 mg (0.58 mmol) of 2-(2,4-Dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl acetamide in 3 mL of DMF at 0° C. is added 127 mg (0.70 mmol, 1.2 equiv) of sodium hydride (60% dispersion in mineral oil). The resulting solution is stirred 10 min, then 95 mL (0.64 mmol, 1.1 equiv) of trans-cinnamyl bromide is added. The reaction mixture is stirred 10 min at 0° C. then 2 h at RT and quenched with 1 mL H2O. The reaction mixture is diluted with 40 mL EtOAc and washed with 40 mL H2O. The organic layer is dried (MgSO4) and the solvents removed in vacuo. Purification of the resulting oil by silica gel flash column chromatography using hexane/EtOAc 4/1 as eluent followed by lyophilization of the product afforded 262 mg of the 2-[2,4-Dioxo-5-phenyl-3-(3-phenyl-allyl)-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-phenyl acetamide as a white amorphous solid: 1H NMR (CDCl3, 300 MHz) δ7.46-7.07 (m, 18H), 6.92 (dd, 1H, J=1.2, 8.1), 6.46 (d, H, J=15.9), 6.25 (m, 1H), 5.04 (m, 1H), 4.31 (d, 1H, J=16.6), 4.13 (d, 1H, J=16.6), 3.46 (dd, 1H, J=6.1, 7.8), 2.93 (m, 2H), 1.10 (2×d, 6H, J=6.9); low resolution MS (FAB) m/e 544 (MH+), 409, 223.

후처리

  1. stirringThe reaction mixture is stirred 10 min at 0° C.
  2. custom2 h at RT and quenched with 1 mL H2O
  3. additionThe reaction mixture is diluted with 40 mL EtOAc
  4. washwashed with 40 mL H2O
  5. dry with materialThe organic layer is dried (MgSO4)
  6. customthe solvents removed in vacuo
  7. customPurification of the resulting oil by silica gel flash column chromatography

출처 및 근거

ORD 기록
ord-0cd653b114b441758a5f255717149de6
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859007

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