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Hydrochloric Acid → [3-Chloro-2-[[4-[(4-chlorophenyl)acetyl]-1-piperazinyl]-methyl]-phenoxy]-acetic Acid

HRID 38258
Notes
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Reaction equation

HRID 38258 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 158793-Chlorophenylacetic acidHCID 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 Acid

Product 1

HCID 11561177[3-Chloro-2-[[4-[(4-chlorophenyl)acetyl]-1-piperazinyl]-methyl]-phenoxy]-acetic Acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. stirringstirred for 3 h
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by RPHPLC

Sources & evidence

ORD record
ord-78899de241734231a9ed10a9819cd875
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524715B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes