Reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[C:4]([CH2:13][N:14]2[CH2:19][CH2:18][N:17](S(C3C=CC=CC=3)(=O)=O)[CH2:16][CH2:15]2)[CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:53][C:54]1[CH:55]=[C:56](CC(O)=O)[CH:57]=[CH:58][CH:59]=1.[OH-].[Na+].[ClH:66].C([O:70][CH2:71][CH3:72])(=O)C>CN(C=O)C>[Cl:66][C:3]1[C:4]([CH2:13][N:14]2[CH2:15][CH2:16][N:17]([C:71](=[O:70])[CH2:72][C:57]3[CH:56]=[CH:55][C:54]([Cl:53])=[CH:59][CH:58]=3)[CH2:18][CH2:19]2)=[C:5]([CH:11]=[CH:12][CH:2]=1)[O:6][CH2:7][C:8]([OH:10])=[O:9]Participants
8
Reactant 6
HCID 313Hydrochloric Acid
HCID 8857Ethyl Acetate
HCID 14798Sodium Hydroxide
HCID 158793-Chlorophenylacetic acid
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 53317503[4-chloro-2-[4-(phenylsulfonyl)-1-piperazinylmethyl]phenoxy]-acetic AcidProduct 1
Reagents, catalysts & solvents 1
Procedure
The product from Example 11 part (a) (300 mg) was dissolved in DMF (10 ml) and treated with HATU ((570 mg), followed by 3-chlorobenzeneacetic acid (190 mg). The reaction mixture was stirred for 18 h, treated with 1M NaOH (3 ml) and stirred for 3 h. The reaction was acidified with 2M HCl, diluted with ethyl acetate, washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by RPHPLC to give the title compound (110 mg).
Workup
- stirringstirred for 3 h
- washwashed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe residue was purified by RPHPLC
Sources & evidence
- ORD record
- ord-78899de241734231a9ed10a9819cd875
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524715B2
Linked notes
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