Diisopropylethylamine → 8-Hydroxy-2-oxo-2H-chromene-3-carboxylic acid (4'-Methoxy-biphenyl-3-yl)-amide

HRID 240052

반응식

HRID 240052 반응식
CCN(C(C)C)C(C)C.[OH:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:20]=1[O:19][C:18](=[O:21])[C:17]([C:22]([OH:24])=O)=[CH:16]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:49][O:50][C:51]1[CH:56]=[CH:55][C:54]([C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([NH2:63])[CH:58]=2)=[CH:53][CH:52]=1>CN(C=O)C>[CH3:49][O:50][C:51]1[CH:52]=[CH:53][C:54]([C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([NH:63][C:22]([C:17]3[C:18](=[O:21])[O:19][C:20]4[C:15]([CH:16]=3)=[CH:14][CH:13]=[CH:12][C:11]=4[OH:10])=[O:24])[CH:58]=2)=[CH:55][CH:56]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 27595634'-Methoxy(1,1'-biphenyl)-3-amineHCID 72457168-Hydroxy-3-carboxy-coumarinHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 441975228-Hydroxy-2-oxo-2H-chromene-3-carboxylic acid (4'-Methoxy-biphenyl-3-yl)-amide수율 52%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

DIEA (0.0144 mL, 0.083 mmol) was added to 8-hydroxy-3-carboxy-coumarin (0.016 g, 0.075 mmol) and HATU (0.032 g, 0.083 mmol) in 0.36 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 4′-Methoxy-biphenyl-3-ylamine (0.015 g, 0.075 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 and the solvent removed under vacuum to give 0.015 g of product in 52% yield: LCMS (ESI) m/z 388 (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. customthe solvent removed under vacuum

출처 및 근거

ORD 기록
ord-aec94bfb008b44fd86ccb93b9515c315
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642788B2

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