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

HRID 240124Notes

Reaction equation

HRID 240124 reaction equation
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.[N:49]1([S:55]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[C:64]2[CH:69]=[CH:68][CH:67]=[C:66]([NH2:70])[CH:65]=2)(=[O:57])=[O:56])[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1>CN(C=O)C>[N:49]1([S:55]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[C:64]2[CH:69]=[CH:68][CH:67]=[C:66]([NH:70][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:65]=2)(=[O:57])=[O:56])[CH2:50][CH2:51][O:52][CH2:53][CH2:54]1

Participants

6

Reactant 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 668647442'-(Morpholine-4-sulfonyl)-biphenyl-3-ylamine

Product 1

HCID 866504218-Hydroxy-2-oxo-2H-chromene-3-carboxylic acid (2'-(Morpholine-4-sulfonyl)-biphenyl-3-yl)-amideYield 54.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (0.009 mL, 0.052 mmol) was added to 8-hydroxy-3-carboxy-coumarin (0.010 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 and the solvent removed under vacuum to give 0.013 g of product in 53% yield: LCMS (ESI) m/z 507 (MH+).

Workup

  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

Sources & evidence

ORD record
ord-fa7ec041528f40d0b13e894f4df924f3
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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