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Diisopropylethylamine → 8-Hydroxy-2-oxo-2H-chromene-3-carboxylic acid [3-(6-methoxy-naphthalen-2-yl)-phenyl]-amide

HRID 240096
ノート
印刷プレビュー

反応式

HRID 240096 の反応式
C(N(C(C)C)CC)(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]2[C:58](=[CH:59][CH:60]=1)[CH:57]=[C:56]([C:61]1[CH:62]=[C:63]([NH2:67])[CH:64]=[CH:65][CH:66]=1)[CH:55]=[CH:54]2>CN(C)C=O>[CH3:49][O:50][C:51]1[CH:52]=[C:53]2[C:58](=[CH:59][CH:60]=1)[CH:57]=[C:56]([C:61]1[CH:62]=[C:63]([NH:67][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:64]=[CH:65][CH:66]=1)[CH:55]=[CH:54]2
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 227240743-(6-Methoxynaphthalen-2-yl)aniline

生成物 1

HCID 866504008-Hydroxy-2-oxo-2H-chromene-3-carboxylic acid [3-(6-methoxy-naphthalen-2-yl)-phenyl]-amide
収率 38.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Diisopropylethylamine (DIEA, 0.0115 mL, 0.067 mmol) was added to 8-hydroxy-3-carboxy-coumarin (0.012 g, 0.06 mmol) and O-(7-Azabenzotriazole-1-yl)-N,N,N,N′-tetramethyluronium hexafluorophosphate (HATU, 0.025 g, 0.067 mmol) in 0.5 mL of dimethylformamide (DMF) with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-(6-methoxy-naphthalen-2-yl)-phenylamine (0.015 g, 0.06 mmol) was added and allowed to react overnight. DMF was removed under vacuum and the reaction was resuspended in dimethylsulfoxide (DMSO). The crude product was purified on a Parallex Flex parallel preparative reverse phase HPLC instrument (Biotage) using a solvent gradient of 10-95% acetonitrile (ACN)/H2O with 0.05% trifluoroacetic acid (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. Solvent was removed under vacuum and the resulting solid was left overnight in vacuo to give 0.010 g of product in 38% yield: LCMS (ESI) m/z 438 (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. customSolvent was removed under vacuum

出典と根拠

ORDレコード
ord-585bc7548e2c485fb434bfbcaa007ec0
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

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