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Toluene → HCID 67215620、化合物

HRID 472905
ノート
印刷プレビュー

反応式

HRID 472905 の反応式
C([N:3](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:25][O:26][C:27]([C:29]1[CH:30]=[C:31]([CH:46]=[CH:47][C:48]=1[N+:49]([O-:51])=[O:50])[C:32]([C:34]1[N:38]2[CH:39]=[C:40](C(O)=O)[CH:41]=[CH:42][C:37]2=[CH:36][N:35]=1)=[O:33])=[O:28].[C:52](=[O:55])(O)[O-:53].[Na+].[C:57]1([CH3:63])[CH:62]=CC=C[CH:58]=1>O.C(O)(C)(C)C>[C:57]([O:53][C:52]([NH:3][C:40]1[CH:41]=[CH:42][C:37]2[N:38]([C:34]([C:32]([C:31]3[CH:46]=[CH:47][C:48]([N+:49]([O-:51])=[O:50])=[C:29]([CH:30]=3)[C:27]([O:26][CH3:25])=[O:28])=[O:33])=[N:35][CH:36]=2)[CH:39]=1)=[O:55])([CH3:63])([CH3:62])[CH3:58]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 1140TolueneHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 67215444HCID 67215444、化合物

生成物 1

HCID 67215620HCID 67215620、化合物

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6386tert-Butanol溶媒

反応条件

温度
110 °C

実験手順

0.55 ml (3.96 mmol) of triethylamine and 1.07 ml of tert-butanol, followed by 0.31 ml (1.40 mmol) of diphenylphosphoryl azide, are added to 430 mg (1.16 mmol) of 3-[3-(methoxycarbonyl)-4-nitrobenzoyl]imidazo[1,5-a]pyridine-6-carboxylic acid in 20 ml of toluene. The reaction medium is heated at 110° C. for 3 hours and then cooled to ambient temperature. Water and a saturated aqueous sodium bicarbonate solution are added and then the extraction is carried out with ethyl acetate. The organic phase is separated by settling, washed with a saturated aqueous sodium chloride solution, then dried over sodium sulfate and concentrated under reduced pressure. The product is purified by column chromatography on silica gel, elution being carried out with a mixture of dichloromethane and methanol (98/2). 480 mg of an orange-colored solid are obtained. Melting point: 182° C.; 1H NMR (d6-DMSO): 1.55 (9H, s), 3.92 (3H, s), 7.45 (1H, d), 7.90 (1H, s), 7.99 (1H, d), 8.24 (1H, d), 8.67 (1H, d), 8.76 (1H, s), 9.89 (1H, s)

後処理

  1. temperaturecooled to ambient temperature
  2. extractionthe extraction
  3. customThe organic phase is separated
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe product is purified by column chromatography on silica gel, elution
  8. additionbeing carried out with a mixture of dichloromethane and methanol (98/2)

出典と根拠

ORDレコード
ord-5cd55df8324748b387248b05bd91bb71
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08633216B2

反応ノート

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