Triethylamine → 2-(4-tert-Butylphenyl)-N-((3,4-difluorophenyl){1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)acetamide

HRID 877379

Reaktionsgleichung

Reaktionsgleichung von HRID 877379
[Cl-].[F:2][C:3]1[CH:4]=[C:5]([CH:10]([C:12]2[N:13]=[N:14][N:15]([CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:16]=2)[NH3+:11])[CH:6]=[CH:7][C:8]=1[F:9].[C:22]([C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33](O)=[O:34])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23].Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>O.C(Cl)Cl>[C:22]([C:26]1[CH:27]=[CH:28][C:29]([CH2:32][C:33]([NH:11][CH:10]([C:5]2[CH:6]=[CH:7][C:8]([F:9])=[C:3]([F:2])[CH:4]=2)[C:12]2[N:13]=[N:14][N:15]([CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:16]=2)=[O:34])=[CH:30][CH:31]=1)([CH3:25])([CH3:23])[CH3:24]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 118343Benzeneacetic acid, 4-(1,1-dimethylethyl)-HCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86668966(3,4-difluorophenyl){1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methanaminium chloride

Produkt 1

HCID 671758872-(4-tert-Butylphenyl)-N-((3,4-difluorophenyl){1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)acetamideAusbeute 75,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a 50 ml round bottom flask equipped with a magnetic-stir bar were added (3,4-difluorophenyl){1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methanaminium chloride (0.500 g, 1.502 mmol), 4-tert-butylphenylacetic acid (0.289 mg, 1.502 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.288 g, 1.502 mmol), 1-hydroxy-7-azabenzotriazole (0.204 mg, 1.502 mmol) and triethylamine (0.629 ml, 2.253 mmol) into 10.0 ml of CH2Cl2. The resulting solution was stirred at room temperature for 2 hours. The reaction mixture was diluted with water and the two layers were separated. The aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuum. Purification by preparative HPLC (20-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column) to afford 0.536 g (67%) of the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.347 (m, 2H), 7.190 (m, 3H), 7.040 (m, 2H), 6.970 (m, 2H), 6.223 (d, J=7.60 Hz, 1H), 3.852 (ABq, J=15.29 Hz, 2H), 3.580 (s, 2H), 1.305 (s, 9H), 0.125 (s, 9H). ES-MS [M+1]+: 471.2.

Aufarbeitung

  1. customTo a 50 ml round bottom flask equipped with a magnetic-stir bar
  2. customthe two layers were separated
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuum
  8. customPurification
  9. additionby preparative HPLC (20-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column)

Quellen und Nachweise

ORD-Eintrag
ord-e151b7be13bc499a9a05c452b1f40df8
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987310B2

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