Diisopropylethylamine → 6-[(1-Methoxy-2-methylindolizin-3-yl)carbonyl]-3-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]quinazoline-2,4(1H,3H)-dione

HRID 535444ノート

反応式

HRID 535444 の反応式
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[OH:34]/[N:35]=[C:36](/[NH2:38])\[CH3:37].[CH3:39][O:40][C:41]1[C:42]([CH3:69])=[C:43]([C:50]([C:52]2[CH:53]=[C:54]3[C:59](=[CH:60][CH:61]=2)[NH:58][C:57](=[O:62])[N:56]([CH2:63][C:64](OC)=O)[C:55]3=[O:68])=[O:51])[N:44]2[C:49]=1[CH:48]=[CH:47][CH:46]=[CH:45]2>CN(C=O)C.O>[CH3:39][O:40][C:41]1[C:42]([CH3:69])=[C:43]([C:50]([C:52]2[CH:53]=[C:54]3[C:59](=[CH:60][CH:61]=2)[NH:58][C:57](=[O:62])[N:56]([CH2:63][C:64]2[O:34][N:35]=[C:36]([CH3:37])[N:38]=2)[C:55]3=[O:68])=[O:51])[N:44]2[C:49]=1[CH:48]=[CH:47][CH:46]=[CH:45]2

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 5360664N'-hydroxyethanimidamideHCID 66653305Methyl {6-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]-2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl}acetate

生成物 1

HCID 565982206-[(1-Methoxy-2-methylindolizin-3-yl)carbonyl]-3-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]quinazoline-2,4(1H,3H)-dione収率 41.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

0.14 g (0.37 mmol) of HBTU, 0.21 ml (1.23 mmol) of DIEA and then 0.18 g (1.23 mmol) of (1E)-N′-hydroxyethanimidamide are added, under an inert atmosphere at ambient temperature, to 0.1 g (0.25 mmol) of methyl {6-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]-2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl}acetate in 5 ml of DMF. The reaction medium is heated at 90° C. for 24 hours. After hydrolysis with water, the reaction medium is extracted with ethyl acetate. The organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate and then with water, dried over sodium sulphate, filtered, and then concentrated under reduced pressure. The yellow solid obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (95/5) mixture. 0.046 g of a yellow solid is obtained.

後処理

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. washThe organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate
  3. dry with materialwith water, dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe yellow solid obtained
  7. customis purified by silica gel column chromatography, elution

出典と根拠

ORDレコード
ord-c927bf85d99947f5940efc6ecd6e6a1b
出典データセット
uspto-grants-2014_10
特許番号
US08859544B2

反応ノート

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