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

HRID 38258

Reaktionsgleichung

Reaktionsgleichung von HRID 38258
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]

Komponenten

8

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-78899de241734231a9ed10a9819cd875
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524715B2

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