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

反応式

HRID 343110 の反応式
[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

参加物

5

反応物 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

生成物 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 acetamide収率 83.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0cd653b114b441758a5f255717149de6
出典データセット
uspto-grants-1999_01
特許番号
US05859007

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