Diethylamine → 7-Acetamido-N,N-diethyl-9-oxo-9H-xanthene-3-carboxamide

HRID 733058Notes

Reaction equation

HRID 733058 reaction equation
[C:1]([NH:4][C:5]1[CH:18]=[C:17]2[C:8]([O:9][C:10]3[CH:11]=C(C(O)=O)[CH:13]=[CH:14][C:15]=3[C:16]2=[O:19])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].CN(C([O:30]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(NCC)C.[CH:52]([N:55]([CH:58]([CH3:60])C)[CH2:56][CH3:57])([CH3:54])C>CN(C=O)C.O>[CH2:58]([N:55]([CH2:56][CH3:57])[C:52]([C:54]1[CH:13]=[CH:14][C:15]2[C:16](=[O:19])[C:17]3[C:8]([O:9][C:10]=2[CH:11]=1)=[CH:7][CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:18]=3)=[O:30])[CH3:60]

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57839203HCID 57839203, compound

Product 1

HCID 667020647-Acetamido-N,N-diethyl-9-oxo-9H-xanthene-3-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Compound 6f (2 g, 6.7 mmol) in 35 mL of DMF was treated with HATU (2.5 g, 6.7 mmol), diethylamine (0.2 mL, 8.7 mmol), and diisopropylethylamine (4.75 mL, 26.8 mmol). After stirring for 3 h the reaction was poured into water and the solid was collected to give the product, compound 7f. The filtrate was extracted with diethyl ether/THF (1:1). The combined organic phases were washed with water, brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo and combined with the above solid to give 1.5 g total of compound 7f. MS m/z=353 (M+1). 7-Acetylamino-9-hydroxy-9-(1-methyl-piperidin-4-yl)-9H-xanthene-3-carboxylic acid diethylamide, 8f

Workup

  1. customthe solid was collected

Sources & evidence

ORD record
ord-b933d394094b4449af73040fde19af1e
Source dataset
uspto-grants-2009_09
Patent number
US07589103B2

Reaction notes

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