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

HRID 240121Notes

Reaction equation

HRID 240121 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[O:20][C:19](=[O:22])[C:18]([C:23]([OH:25])=O)=[CH:17]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:50][C:51]1[CH:52]=[C:53]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[NH:63][C:64](=[O:66])[CH3:65])[CH:54]=[CH:55][CH:56]=1>CN(C=O)C>[C:64]([NH:63][C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][C:57]=1[C:53]1[CH:54]=[CH:55][CH:56]=[C:51]([NH:50][C:23]([C:18]2[C:19](=[O:22])[O:20][C:21]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][C:12]=3[O:11][CH3:10])=[O:25])[CH:52]=1)(=[O:66])[CH3:65]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2345628-Methoxy-2-oxo-2H-chromene-3-carboxylic acidHCID 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 866504198-Methoxy-2-oxo-2H-chromene-3-carboxylic acid (2'-acetylamino-biphenyl-3-yl)-amideYield 70.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (0.013 mL, 0.073 mmol) was added to 8-methoxy-3-carboxy-coumarin (0.015 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 when a solid precipitated out of solution. The resulting precipitate was filtered, dried under suction, and finally dried overnight in vacuo to give 0.020 g of product in 69% yield: LCMS (ESI) m/z 429 (MH+).

Workup

  1. customresulted
  2. customto react overnight when a solid
  3. customprecipitated out of solution
  4. filtrationThe resulting precipitate was filtered
  5. customdried under suction, and finally dried overnight in vacuo

Sources & evidence

ORD record
ord-b167819d47f34bb182ea1d2f074a4322
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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