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Diisopropylethylamine → 8-Trifluoromethoxy-2-oxo-2H-chromene-3-carboxylic acid (2'-(Morpholine-4-sulfonyl)-biphenyl-3-yl)-amide

HRID 240126
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HRID 240126 반응식
CCN(C(C)C)C(C)C.[F:10][C:11]([F:28])([F:27])[O:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[O:21][C:20](=[O:23])[C:19]([C:24]([OH:26])=O)=[CH:18]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:53]1([S:59]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][C:63]=2[C:68]2[CH:73]=[CH:72][CH:71]=[C:70]([NH2:74])[CH:69]=2)(=[O:61])=[O:60])[CH2:58][CH2:57][O:56][CH2:55][CH2:54]1>CN(C=O)C>[N:53]1([S:59]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][C:63]=2[C:68]2[CH:73]=[CH:72][CH:71]=[C:70]([NH:74][C:24]([C:19]3[C:20](=[O:23])[O:21][C:22]4[C:17]([CH:18]=3)=[CH:16][CH:15]=[CH:14][C:13]=4[O:12][C:11]([F:10])([F:28])[F:27])=[O:26])[CH:69]=2)(=[O:61])=[O:60])[CH2:54][CH2:55][O:56][CH2:57][CH2:58]1
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참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668647442'-(Morpholine-4-sulfonyl)-biphenyl-3-ylamineHCID 866503588-Trifluoromethoxy-3-carboxy-coumarin

생성물 1

HCID 86650422
8-Trifluoromethoxy-2-oxo-2H-chromene-3-carboxylic acid (2'-(Morpholine-4-sulfonyl)-biphenyl-3-yl)-amide
수율 51.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

DIEA (0.009 mL, 0.052 mmol) was added to 8-trifluoromethoxy-3-carboxy-coumarin (0.013 g, 0.047 mmol) and HATU (0.020 g, 0.052 mmol) in 0.36 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 2′-(Morpholine-4-sulfonyl)-biphenyl-3-ylamine (0.015 g, 0.047 mmol) was added and allowed to react overnight. DMF was removed under vacuum and the reaction was resuspended in DMSO. The crude product was purified on a Parallex Flex parallel preparative reverse phase HPLC instrument (Biotage) using a solvent gradient of 10-95% ACN/H2O with 0.05% TFA at a flow rate of 20 mL/min. UV absorbance was monitored at 254 nm and the fractions corresponding to the product peak were collected were collected and the solvent removed under vacuum to give 0.014 g of product in 50% yield: LCMS (ESI) m/z 591 (MH+).

후처리

  1. customresulted
  2. customto react overnight
  3. customDMF was removed under vacuum
  4. customThe crude product was purified on a Parallex Flex parallel preparative reverse phase HPLC instrument (Biotage)
  5. customthe fractions corresponding to the product peak were collected
  6. customwere collected
  7. customthe solvent removed under vacuum

출처 및 근거

ORD 기록
ord-40cfe57b22024436bc4f6ea800c97387
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08642788B2

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