ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Dimethylformamide → 3-(4,4'-Dimethoxybenzhydryl)-6-(N-methyl-N-isobutyrylcarbamoyl)-amino-2-propyl-quinazolin-4(3H)-one

HRID 1770146
ノート
印刷プレビュー

反応式

HRID 1770146 の反応式
[H-].[Na+].N[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([CH2:14][CH2:15][CH3:16])[N:8]([CH:17]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[C:7]2=[O:34].[CH2:35]([O:39]C(Cl)=O)[CH:36]([CH3:38])[CH3:37].C[Si](C)(C)[N-:45][Si](C)(C)C.[Li+].IC.[CH3:55][N:56]([CH:58]=[O:59])C>C1COCC1.CCOC(C)=O>[CH3:33][O:32][C:29]1[CH:28]=[CH:27][C:26]([CH:17]([N:8]2[C:7](=[O:34])[C:6]3[C:11](=[CH:12][CH:13]=[C:4]([C:58](=[O:59])[N:56]([CH3:55])[C:35](=[O:39])[CH:36]([CH3:37])[CH3:38])[C:5]=3[NH2:45])[N:10]=[C:9]2[CH2:14][CH2:15][CH3:16])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:31][CH:30]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 6

HCID 6228Dimethylformamide2 回HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 62365Isobutyl chloroformateHCID 2733832Lithium hexamethyldisilazaneHCID 19934842HCID 19934842、化合物

生成物 1

HCID 67789925
3-(4,4'-Dimethoxybenzhydryl)-6-(N-methyl-N-isobutyrylcarbamoyl)-amino-2-propyl-quinazolin-4(3H)-one
収率 71%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of 81.5 mg (2.7 mmol) of 80% NaH in 3 ml of dry DMF at 0° C. under nitrogen was added dropwise a solution of 1.03 g (2.5 mmol) of 6-amino-3-(4,4'-dimethoxybenzhydryl)-2-propyl-quinazolin-4(3H)-one dissolved in 3 ml of DMF. The resulting mixture was stirred for 30 minutes and was then treated with 0.35 ml (2.7 mmol) of isobutylchloroformate neat. The solution was stirred for 30 minutes and then treated with 2.97 ml (2.97 mmol) of a 1M solution of lithium hexamethyldisilazide in THF. The dark solution was stirred for a further 30 minutes at 0° C. and then was treated with 0.2 ml (3.26 mmol) of iodomethane neat. The mixture was stirred overnight at room temperature, poured into 50 ml of EtOAc and washed consecutively with water (2×10 ml), brine (1×10 ml) and dried over MgSO4 . The product was purified by flash chromatography over silica gel eluting with 30% EtOAc/hexanes to give 0.9 g (1.7 mmol) of an oil. 71% yield. 1H-NMR (CDCl3): 0.82-0.91 (m, 6H), 0.96 (d, 3H, J=6.8 Hz), 1.52 (m, 2H), 1.88 (m, 1H), 2.67 (bt, 2H), 3.35 (s, 3H), 3.80 (s, 6H), 3.90 (d, 2H, J=6.6 Hz), 6.87 (d, 4H, J=8.8 Hz), 7.20 (d, 4H, J=8.8 Hz), 7.61 (m, 1H), 7.78 (m, 1H), 8.01 (d, 1H, 2 Hz).

後処理

  1. stirringThe solution was stirred for 30 minutes
  2. stirringThe dark solution was stirred for a further 30 minutes at 0° C.
  3. stirringThe mixture was stirred overnight at room temperature
  4. washwashed consecutively with water (2×10 ml), brine (1×10 ml)
  5. dry with materialdried over MgSO4
  6. customThe product was purified by flash chromatography over silica gel eluting with 30% EtOAc/hexanes

出典と根拠

ORDレコード
ord-353f06e924294ef19b2f9c8a8c555194
出典データセット
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05385894

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート