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

HRID 240064
ノート
印刷プレビュー

反応式

HRID 240064 の反応式
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:52]=[C:53]([C:59]2[CH:64]=[CH:63][CH:62]=[C:61]([NH2:65])[CH:60]=2)[CH:54]=[CH:55][C:56]=1[O:57][CH3:58]>CN(C=O)C>[CH3:49][O:50][C:51]1[CH:52]=[C:53]([C:59]2[CH:64]=[CH:63][CH:62]=[C:61]([NH:65][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:60]=2)[CH:54]=[CH:55][C:56]=1[O:57][CH3:58]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 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)HCID 392318553',4'-Dimethoxy-[1,1'-biphenyl]-3-amine

生成物 1

HCID 866503768-Hydroxy-2-oxo-2H-chromene-3-carboxylic acid (3',4'-Dimethoxy-biphenyl-3-yl)-amide
収率 19%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

DIEA (0.013 mL, 0.072 mmol) was added to 8-hydroxy-3-carboxy-coumarin (0.014 g, 0.065 mmol) and HATU (0.027 g, 0.072 mmol) in 0.36 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3′,4′-Dimethoxy-biphenyl-3-ylamine (0.015 g, 0.065 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 0.005 g of product in 19% yield: LCMS (ESI) m/z 418 (MH+).

後処理

  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

出典と根拠

ORDレコード
ord-3e808c9ff26f42c19c3c13076553fa19
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08642788B2

反応ノート

読み込み中…

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