Diethylamine → 5-Methoxy-9-oxo-9H-xanthene-3-carboxylic acid diethylamide

HRID 733396Notes

Reaction equation

HRID 733396 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[O:5][C:6]1[CH:7]=C(C(O)=O)[CH:9]=[CH:10][C:11]=1[C:12]2=[O:17].CN(C([O:28]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:45]([N:48]([CH:51]([CH3:53])C)[CH2:49][CH3:50])([CH3:47])C.C(NCC)C>CN(C=O)C>[CH2:51]([N:48]([CH2:49][CH3:50])[C:45]([C:47]1[CH:9]=[CH:10][C:11]2[C:12](=[O:17])[C:13]3[C:4]([O:5][C:6]=2[CH:7]=1)=[C:3]([O:2][CH3:1])[CH:16]=[CH:15][CH:14]=3)=[O:28])[CH3:53]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 574366735-methoxy-9-oxo-9H-xanthene-3-carboxylic acid2×

Product 1

HCID 578392345-Methoxy-9-oxo-9H-xanthene-3-carboxylic acid diethylamideYield 96.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-methoxy-9-oxo-9H-xanthene-3-carboxylic acid, 3c (6.8 g, 25.2 mmol) in DMF (70 mL), were added HBTU (10 g, 26.4 mmol) and N,N-diisopropyl-N-ethylamine (5.27 mL, 30.2 mmol). The mixture was stirred for 15 min at rt. N,N-Diethylamine (3.12 mL, 30.2 mmol) was added, and the mixture was stirred for 4 h at rt. The mixture was poured into ice-water (300 mL), and a solid precipitated. The solid was separated via filtration, washed with H2O, and air-dried. The solid was purified via flash column chromatography (eluent gradient: 1% MeOH in CH2Cl2 to 5% MeOH in CH2Cl2) to yield 7.93 g (96.7%) of title compound 5-methoxy-9-oxo-9H-xanthene-3-carboxylic acid diethylamide, 4c. MS m/z=326.0 (MH+).

Workup

  1. stirringthe mixture was stirred for 4 h at rt
  2. customa solid precipitated
  3. customThe solid was separated via filtration
  4. washwashed with H2O
  5. customair-dried
  6. customThe solid was purified via flash column chromatography (eluent gradient: 1% MeOH in CH2Cl2 to 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-7ee9fd8561844bd0808af56cc8f8280e
Source dataset
uspto-grants-2009_09
Patent number
US07589104B2

Reaction notes

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