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Water → 2-Aminocarbonylamino-6-azidomethylindole-3-carboxamide

HRID 216642
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HRID 216642 반응식
C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2.[NH2:29][C:30]([NH:32][C:33]1[NH:34][C:35]2[C:40]([C:41]=1[C:42]([NH2:44])=[O:43])=[CH:39][CH:38]=[C:37]([CH2:45]O)[CH:36]=2)=[O:31].O>O1CCCC1>[NH2:29][C:30]([NH:32][C:33]1[NH:34][C:35]2[C:40]([C:41]=1[C:42]([NH2:44])=[O:43])=[CH:39][CH:38]=[C:37]([CH2:45][N:15]=[N+:16]=[N-:17])[CH:36]=2)=[O:31]
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참가 물질

6

반응물 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 249894282-Aminocarbonylamino-6-hydroxymethylindole-3-carboxamide2회

생성물 1

HCID 591899312-Aminocarbonylamino-6-azidomethylindole-3-carboxamide수율 11.4%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

Diphenylphosphoryl azide (42 μL, 0.19 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (29 μL, 0.19 mmol) were added to a solution of 2-aminocarbonylamino-6-hydroxymethylindole-3-carboxamide (Compound 16-1, 40 mg, 0.16 mmol) in anhydrous tetrahydrofuran (5 mL) under ice-cooling, the mixture was stirred at room temperature overnight. Water (10 mL) was added to the reaction mixture, and the whole was extracted with ethyl acetate (10 mL). The organic layer was washed with brine (20 mL) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (5.0 mg) as a yellow solid (yield 11%).

후처리

  1. temperaturecooling
  2. extractionthe whole was extracted with ethyl acetate (10 mL)
  3. washThe organic layer was washed with brine (20 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-44e89feb11b249e19d66e80b05704a5b
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08193237B2

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