2-Dimethylaminopyridine → N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-chloro-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)-1-methyl-1H-imidazole-4-sulfonamide

HRID 1368616Notes

Reaction equation

HRID 1368616 reaction equation
CN1C=C(S(Cl)(=O)=O)N=C1.O1C2C=CC(C3C(OCCOC4N=CC(Cl)=CN=4)=NN(C)C=3N)=CC=2OC1.CN(C1C=CC=CN=1)C.[O:47]1[C:51]2[CH:52]=[CH:53][C:54]([C:56]3[C:57]([O:81][CH2:82][CH2:83][O:84][C:85]4[N:90]=[CH:89][C:88]([Cl:91])=[CH:87][N:86]=4)=[N:58][N:59]([CH3:80])[C:60]=3[N:61](S(C3N=CN(C)C=3)(=O)=O)[S:62]([C:65]3[N:66]=[CH:67][N:68]([CH3:70])[CH:69]=3)(=[O:64])=[O:63])=[CH:55][C:50]=2[O:49][CH2:48]1>N1C=CC=CC=1>[O:47]1[C:51]2[CH:52]=[CH:53][C:54]([C:56]3[C:57]([O:81][CH2:82][CH2:83][O:84][C:85]4[N:90]=[CH:89][C:88]([Cl:91])=[CH:87][N:86]=4)=[N:58][N:59]([CH3:80])[C:60]=3[NH:61][S:62]([C:65]3[N:66]=[CH:67][N:68]([CH3:70])[CH:69]=3)(=[O:63])=[O:64])=[CH:55][C:50]=2[O:49][CH2:48]1

Participants

6

Reactant 4

HCID 218852-DimethylaminopyridineHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 22281927HCID 22281927, compoundHCID 22281963HCID 22281963, compound

Product 1

HCID 9871777N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-chloro-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)-1-methyl-1H-imidazole-4-sulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Methyl-1H-imidazole-4-sulfonyl chloride (45 mg) was carefully added at room temperature under an atmosphere of nitrogen to a solution of 4-(1,3-benzodioxol-5-yl)-3-{2-[(5-chloro-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-ylamine (Preparation 48) (50 mg) and dimethylaminopyridine (16 mg) in anhydrous pyridine (2.4 ml). The reaction was stirred for two days, then the mixture was concentrated under reduced pressure and a saturated solution of ammonium chloride (6 ml), ethyl acetate (6 ml) and brine (6 ml) were sequentially added. The aqueous phase was extracted with ethyl acetate (2×8 ml) and the combined organic phases were washed with brine (10 ml), dried over sodium sulfate and concentrated under reduced pressure. The black residue was purified by preparative TLC (silica) eluted with dichloromethane:methanol (95:5) yielding a mixture of title compound and N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-chloro-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)-1-methyl-N-[(1-methyl-1H-imidazol-4-yl)sulfonyl]-1H-imidazole-4-sulfonamide. The title compound was purified by HPLC (5.4 mg).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additiona saturated solution of ammonium chloride (6 ml), ethyl acetate (6 ml) and brine (6 ml) were sequentially added
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×8 ml)
  4. washthe combined organic phases were washed with brine (10 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe black residue was purified by preparative TLC (silica)
  8. washeluted with dichloromethane:methanol (95:5)
  9. customyielding

Sources & evidence

ORD record
ord-462f35330c6649ff82135762302ec8a8
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

Loading…