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

HRID 240120Notes

Reaction equation

HRID 240120 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.[NH2:49][C:50]1[CH:51]=[C:52]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=2[NH:62][C:63](=[O:65])[CH3:64])[CH:53]=[CH:54][CH:55]=1>CN(C=O)C>[C:63]([NH:62][C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=1[C:52]1[CH:53]=[CH:54][CH:55]=[C:50]([NH:49][C:22]([C:17]2[C:18](=[O:21])[O:19][C:20]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][C:11]=3[OH:10])=[O:24])[CH:51]=1)(=[O:65])[CH3:64]

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 66865485HCID 66865485, compound

Product 1

HCID 866504188-Hydroxy-2-oxo-2H-chromene-3-carboxylic acid (2'-acetylamino-biphenyl-3-yl)-amideYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (0.013 mL, 0.073 mmol) was added to 8-hydroxy-3-carboxy-coumarin (0.014 g, 0.066 mmol) and HATU (0.028 g, 0.073 mmol) in 0.36 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, N-(3′-Amino-biphenyl-2-yl)-acetamide (0.015 g, 0.066 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 0.007 g of product in 27% yield: LCMS (ESI) m/z 415 (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-e1ac3189a54d4680a9829801b591ca58
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

Loading…