Dimethylamine → 6-Iodo-4-methoxy-quinoline-3-carboxylic acid dimethylamide

HRID 1297623Notes

Reaction equation

HRID 1297623 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](O)=[O:13])=[C:5]2[O:15][CH3:16].[CH3:17][NH:18][CH3:19].O1CCCC1.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[CH3:17][N:18]([CH3:19])[C:12]([C:6]1[CH:7]=[N:8][C:9]2[C:4]([C:5]=1[O:15][CH3:16])=[CH:3][C:2]([I:1])=[CH:11][CH:10]=2)=[O:13]

Participants

8

Reactant 6

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 585858316-Iodo-4-methoxy-quinoline-3-carboxylic acid

Product 1

HCID 585858426-Iodo-4-methoxy-quinoline-3-carboxylic acid dimethylamideYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To the mixture of 6-iodo-4-methoxy-quinoline-3-carboxylic acid (example 1b) (1.5 g, 4.56 mmol), 2 M dimethylamine in THF (tetrahydrofuran) (9.11 mL, 18.2 mmol), HOBt (0.74 g, 5.5 mmol) and DIEA (diisopropylethylamine) (2.38 mL, 13.7 mmol) in DMF (N,N-dimethylformamide) (40 mL) was slowly added the solution of O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU) (2.08 g, 5.47 mmol) in DMF (10 mL). After stirring at room temperature for 3 hours, the product was extracted with methylene chloride (2×100 mL). The combined organic layers were successively washed with a saturated aqueous sodium bicarbonate solution (3×50 mL) and water (3×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, using ethyl acetate as eluant) afforded 6-iodo-4-methoxy-quinoline-3-carboxylic acid dimethylamide (1.27 g, 78%) as a solid. LC-MS m/e 357 (MH+).

Workup

  1. extractionthe product was extracted with methylene chloride (2×100 mL)
  2. washThe combined organic layers were successively washed with a saturated aqueous sodium bicarbonate solution (3×50 mL) and water (3×50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a601febe19842a2a09c7f1fdca10ad8
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

Loading…