1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-methyl-N-(thietan-3-yl)-4-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzamide

HRID 1692567Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1692567
Br.[S:2]1[CH2:5][CH:4]([NH2:6])[CH2:3]1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH3:30][C:31]1[CH:39]=[C:38]([C:40]2[CH2:41][C:42]([C:49]3[CH:54]=[C:53]([Cl:55])[C:52]([Cl:56])=[C:51]([Cl:57])[CH:50]=3)([C:45]([F:48])([F:47])[F:46])[CH2:43][N:44]=2)[CH:37]=[CH:36][C:32]=1[C:33](O)=[O:34]>CN(C)C=O.C(N(CC)CC)C.C(OC)(C)(C)C>[CH3:30][C:31]1[CH:39]=[C:38]([C:40]2[CH2:41][C:42]([C:49]3[CH:50]=[C:51]([Cl:57])[C:52]([Cl:56])=[C:53]([Cl:55])[CH:54]=3)([C:45]([F:46])([F:48])[F:47])[CH2:43][N:44]=2)[CH:37]=[CH:36][C:32]=1[C:33]([NH:6][CH:4]1[CH2:5][S:2][CH2:3]1)=[O:34]

Komponenten

8

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 53346555Thietan-3-amine hydrobromideHCID 582709962-methyl-4-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzoic acid

Produkt 1

HCID 582709782-methyl-N-(thietan-3-yl)-4-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

To a solution of thietan-3-amine hydrobromide in N,N-dimethylformamide, triethylamine was added at 0° C. Then 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (122 mg, 0.53 mmol), 1-hydroxybenzotriazole monohydrate (72 mg, 0.53 mmol), and 2-methyl-4-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzoic acid (200 mg, 0.44 mmol) were added to the solution. The reaction mixture was stirred overnight at room temperature and then diluted with t-BuOMe and washed with 2M HCl, and after that with H2O, saturated NaCl aq. and dried over MgSO4. After evaporation, the residue was purified with chromatography (220 mg, 95%).

Aufarbeitung

  1. washwashed with 2M HCl
  2. dry with materialafter that with H2O, saturated NaCl aq. and dried over MgSO4
  3. customAfter evaporation
  4. customthe residue was purified with chromatography (220 mg, 95%)

Quellen und Nachweise

ORD-Eintrag
ord-39f0117e67a04a6f83a0d669e224091a
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158560B2

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