Pyrrolidine → HCID 57839233, compound

HRID 1987937Notes

Reaction equation

HRID 1987937 reaction equation
[O:1]=[C:2]1[C:15]2[CH:14]=[CH:13][C:12]([C:16](Cl)=[O:17])=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[CH:19]([N:22]([CH:25]([CH3:27])C)CC)([CH3:21])C.N1CCCC1>C(#N)C>[N:22]1([C:16]([C:12]2[CH:13]=[CH:14][C:15]3[C:2](=[O:1])[C:3]4[C:8]([O:9][C:10]=3[CH:11]=2)=[CH:7][CH:6]=[CH:5][CH:4]=4)=[O:17])[CH2:19][CH2:21][CH2:27][CH2:25]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 85559966HCID 85559966, compound

Product 1

HCID 57839233HCID 57839233, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

9-oxo-9H-xanthene-3-carboxylic acid (9 g, 37.4 mmol) was added to thionyl chloride (28 mL, 334 mmol). The mixture was refluxed for 5 h. At that time, the thionyl chloride was removed under vacuum and the remaining residue was diluted with toluene and concentrated to dryness to give 9-oxo-9H-xanthene-3-carbonyl chloride. A portion of 9-oxo-9H-xanthene-3-carbonyl chloride (0.25 g, 0.96 mmol) was dissolved in acetonitrile (7 mL). Diisopropylethylamine (335 μL, 1.9 mmol) was then added to the mixture with the subsequent addition of pyrrolidine (113 μL, 1.3 mmol). After stirring 2 h, the solvent was concentrated and the residue was purified by reverse phase preparative HPLC, using a gradient of acetonitrile (10%- 90%) in water with trifluoroacetic acid (0.1%) to afford the 3-(pyrrolidine-1-carbonyl)-xanthen-9-one. MS m/z (MH+) 294.1.

Workup

  1. concentrationthe solvent was concentrated
  2. customthe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-e84a916a2c704c0aba99c508f878b10c
Source dataset
uspto-grants-2009_06
Patent number
US07553850B2

Reaction notes

Loading…