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Toluene → HCID 67215620, 화합물

HRID 472905
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HRID 472905 반응식
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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 1140TolueneHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 67215444HCID 67215444, 화합물

생성물 1

HCID 67215620HCID 67215620, 화합물

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6386tert-Butanol용매

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온도
110 °C

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-5cd55df8324748b387248b05bd91bb71
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08633216B2

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