Dimethylformamide → N1-(4-Difluoromethoxybenzoyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl]-1,2-benzenediamine Hydrochloride

HRID 427669

Reaktionsgleichung

Reaktionsgleichung von HRID 427669
N1C=CC([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][O:14][C:15]([NH:17][C:18]3[C:19]([NH2:24])=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:16])[CH2:9][CH2:8]2)=CC=1.[F:25][CH:26]([F:37])[O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([OH:34])=O)=[CH:30][CH:29]=1.[ClH:38].CN(C)[CH2:41][CH2:42][CH2:43][N:44]=[C:45]=NCC.[CH3:50]N(C=O)C>>[ClH:38].[F:37][CH:26]([F:25])[O:27][C:28]1[CH:29]=[CH:30][C:31]([C:32]([NH:24][C:19]2[C:18]([NH:17][C:15]([O:14][CH:13]([CH:10]3[CH2:9][CH2:8][NH:7][CH2:12][CH2:11]3)[C:41]3[CH:42]=[CH:43][N:44]=[CH:45][CH:50]=3)=[O:16])=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:34])=[CH:35][CH:36]=1

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 7373604-(Difluoromethoxy)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10829995N2-[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl-1,2-benzenediamine

Produkt 1

HCID 86757561N1-(4-Difluoromethoxybenzoyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl]-1,2-benzenediamine HydrochlorideAusbeute 38 %

Versuchsvorschrift

To a solution of N1-[1-(4-pyridyl)piperidin-4-yl-methoxycarbonyl]-1,2-benzenediamine (0.2 g, 0.6 mmol) and 4-difluoromethoxybenzoic acid (0.23 g, 1.2 mmol) in DMF (10 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.24 g, 1.2 mmol). After stirring overnight, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate (300 mL) and 1 N NaOH (150 ml). The layers were separated and the organic phase was washed with brine, dried with MgSO4, filtered and concentrated in vacuo. The residue was purified by RPHPLC method A and the fractions containing pure product were combined and lypholized to give 123 mg (38%) of the title product as a white solid.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate (300 mL) and 1 N NaOH (150 ml)
  3. customThe layers were separated
  4. washthe organic phase was washed with brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by RPHPLC method A
  9. additionthe fractions containing pure product

Quellen und Nachweise

ORD-Eintrag
ord-ede4f5886f7c4bdca988094cfef1c0e2
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313122B1

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