3-(Dimethylamino)pyrrolidine → HCID 512814, compound

HRID 1080216Notes

Reaction equation

HRID 1080216 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[N:14]2[C:9]([C:10]([CH3:19])=[C:11](Cl)[C:12]([F:17])=[CH:13]2)=[C:8]([CH:20]2[CH2:22][CH2:21]2)[CH:7]=1)=[O:5])C.[CH3:23][N:24]([CH3:30])[CH:25]1[CH2:29][CH2:28][NH:27][CH2:26]1>N1C=CC=CC=1>[C:4]([OH:5])(=[O:3])[CH3:6].[CH3:23][N:24]([CH3:30])[CH:25]1[CH2:29][CH2:28][N:27]([C:11]2[C:12]([F:17])=[CH:13][N:14]3[C:9]([C:10]=2[CH3:19])=[C:8]([CH:20]2[CH2:22][CH2:21]2)[CH:7]=[C:6]([C:4]([OH:3])=[O:5])[C:15]3=[O:16])[CH2:26]1

Participants

4

Reactant 2

HCID 27585193-(Dimethylamino)pyrrolidineHCID 9927245Ethyl 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate

Product 1

HCID 512814HCID 512814, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
60 °C

Procedure

A 81 mg sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, was dissolved in 2.5 mL of dry pyridine under a nitrogen atmosphere. To this solution was added a solution of 114 g of 3-(dimethylamino)pyrrolidine in 2.5 mL of pyridine, and the reaction mixture was heated at 60° C. for 39 hours. The pyridine was removed under vacuum, and the residue was stirred with 1N NaOH in THF/water for at 60° C. for 6 hours. The solution was made acidic with acetic acid, and the product was extracted with chloroform. After drying over MgSO4, the solvent was removed, and the residue was purified by chromatography on silica gel, eluting with 100:40:20:8 chloroform: methanol: acetic acid:water to give the title product. mp 165-170° C. (dec.). MS 374 (M+H)+ ; 1H NMR (D6 -DMSO) δ: 0.53 (m, 2H), 0.82-1.08 (m, 2H), 1.75 (s, 3H), 2.22 (s, 6H), 2.08-2.33 (m, 2H), 2.74 (m, 2H), 3.44-3.94 (m, 5H), 8.01 (br, s, 1H), 8.90 (br s, 1H).

Workup

  1. customThe pyridine was removed under vacuum
  2. extractionthe product was extracted with chloroform
  3. dry with materialAfter drying over MgSO4
  4. customthe solvent was removed
  5. customthe residue was purified by chromatography on silica gel
  6. washeluting with 100:40:20:8 chloroform

Sources & evidence

ORD record
ord-09624807423e435297fc10ccf0300b85
Source dataset
uspto-grants-1996_12
Patent number
US05580872

Reaction notes

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