1,2-Dichloroethane → 2-([(4-Fluorophenyl)methyl]oxy)-N-(3-methyl-4-isoxazolyl)-5-{1-[2-(4-morpholinyl)ethyl]-1H-pyrazol-4-yl}benzamide

HRID 1623866Notes

Reaction equation

HRID 1623866 reaction equation
[CH3:1][C:2]1[C:6]([NH2:7])=[CH:5][O:4][N:3]=1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl.C(N(C(C)C)CC)(C)C.[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][O:39][C:40]2[CH:48]=[CH:47][C:46]([C:49]3[CH:50]=[N:51][N:52]([CH2:54][CH2:55][N:56]4[CH2:61][CH2:60][O:59][CH2:58][CH2:57]4)[CH:53]=3)=[CH:45][C:41]=2[C:42](O)=[O:43])=[CH:34][CH:33]=1>CN(C)C=O>[F:31][C:32]1[CH:33]=[CH:34][C:35]([CH2:38][O:39][C:40]2[CH:48]=[CH:47][C:46]([C:49]3[CH:50]=[N:51][N:52]([CH2:54][CH2:55][N:56]4[CH2:61][CH2:60][O:59][CH2:58][CH2:57]4)[CH:53]=3)=[CH:45][C:41]=2[C:42]([NH:7][C:6]2[C:2]([CH3:1])=[N:3][O:4][CH:5]=2)=[O:43])=[CH:36][CH:37]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 138042843-Methyl-1,2-oxazol-4-amineHCID 671068932-{[(4-fluorophenyl)methyl]oxy}-5-{1-[2-(4-morpholinyl)ethyl]-1H-pyrazol-4-yl}benzoic acid

Product 1

HCID 671074082-([(4-Fluorophenyl)methyl]oxy)-N-(3-methyl-4-isoxazolyl)-5-{1-[2-(4-morpholinyl)ethyl]-1H-pyrazol-4-yl}benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methyl-4-isoxazolamine (38.0 mg, 0.28 mmol), 1-hydroxy-7-azabenzotriazole (30.7 mg, 0.23 mmol), EDC (43.3 mg, 0.23 mmol) and diisopropylethylamine (0.10 ml, 0.56 mmol) were added to a solution of 2-{[(4-fluorophenyl)methyl]oxy}-5-{1-[2-(4-morpholinyl)ethyl]-1H-pyrazol-4-yl}benzoic acid (may be prepared as described in Description 114; 80 mg, 0.19 mmol) in N,N-dimethylformamide (2 ml) and the reaction mixture was stirred at room temperature overnight. The DMF was removed on a buchi. The residue was taken up into ethyl acetate (50 ml) and washed with water (1×25 ml). The ethyl acetate layer was evaporated on a buchi under reduced pressure and the residue was purified using the MDAP. The solid obtained after concentrating the appropriate sample was taken up into ethyl acetate (50 ml) and washed with saturated bicarbonate (10 ml). The organic phase was dried (MgSO4) and evaporated to yield the title compound as a white solid. 15 mg.

Workup

  1. customThe DMF was removed on a buchi
  2. washwashed with water (1×25 ml)
  3. customThe ethyl acetate layer was evaporated on a buchi under reduced pressure
  4. customthe residue was purified
  5. customThe solid obtained
  6. concentrationafter concentrating the appropriate sample
  7. washwashed with saturated bicarbonate (10 ml)
  8. dry with materialThe organic phase was dried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-c7e3a6065299453cb4d707dbe86ed690
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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