Ammonium Chloride → HCID 52933910, Verbindung

HRID 1024476Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1024476
C[Al](C)C.[C:5]([C:7]([C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=O)=[CH:12][CH:11]=1)([CH3:9])[CH3:8])#[N:6].[CH3:20][CH:21]([CH3:44])[CH:22]([NH:27][C:28]([C:30]1[S:31][C:32]([C:35]2[CH:40]=[CH:39][C:38]([N+:41]([O-])=O)=[CH:37][CH:36]=2)=[CH:33][N:34]=1)=[O:29])[C:23]([O:25][CH3:26])=[O:24].[Cl-].[NH4+]>C1(C)C=CC=CC=1.C(Cl)Cl.O>[C:5]([C:7]([C:10]1[CH:11]=[CH:12][C:13]([C:14]([NH:41][C:38]2[CH:39]=[CH:40][C:35]([C:32]3[S:31][C:30]([C:28]([NH:27][CH:22]([CH:21]([CH3:44])[CH3:20])[C:23]([O:25][CH3:26])=[O:24])=[O:29])=[N:34][CH:33]=3)=[CH:36][CH:37]=2)=[O:16])=[CH:18][CH:19]=1)([CH3:8])[CH3:9])#[N:6]

Komponenten

8

Edukt 4

HCID 25517Ammonium ChlorideHCID 14698604Methyl 4-(1-cyano-1-methylethyl)benzoate2×HCID 16682925TrimethylaluminumHCID 67150324Methyl 3-methyl-2-(5-(4-nitrophenyl)thiazole-2-carboxamido)butanoate2×

Produkt 1

HCID 52933910HCID 52933910, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Trimethyl aluminium (0.36 ml, 2M solution in toluene) was added to a solution of methyl 4-(2-cyanopropan-2-yl)benzoate (Intermediate 5, 100 mg) and methyl 2-(5-(4-aminophenyl) thiazole-2-carboxamido)-3-methylbutanoate (Intermediate 2, 150 mg) in toluene (12 ml). The reaction mixture was heated to 80° C. for 4 hours in a sealed tube. Reaction mass was cooled to RT, water was added and neutralized with saturated aqueous solution of ammonium chloride. Methylene chloride was added to it. Organic and aqueous layers were separated. Organic layer was washed successively with 1N HCl, saturated NaHCO3 and brine solution. It was then dried over sodium sulfate and concentrated to obtain dark brown residue which was purified by silica gel column chromatography in EtOAc-Petroleum ether to obtain pale brown solid. The solid was crystallized in CHCl3-petroleum ether to obtain title compound as off white solid. Yield: 75 mg (33%); 1HNMR (DMSO-d6, 300 MHz): δ 10.49 (s, 1H), 8.75 (d, 1H), 8.41 (s, 1H), 8.04 (d, 2H), 7.93 (d, 2H), 7.81 (d, 2H), 7.71 (d, 2H), 4.33 (m, 1H), 3.68 (s, 3H), 2.27 (m, 1H), 1.74 (s, 6H), 0.95 (m, 6H); MS (ES+) m/z 505.2 (M+1).

Aufarbeitung

  1. customReaction mass
  2. temperaturewas cooled to RT
  3. customOrganic and aqueous layers were separated
  4. washOrganic layer was washed successively with 1N HCl, saturated NaHCO3 and brine solution
  5. dry with materialIt was then dried over sodium sulfate
  6. concentrationconcentrated
  7. customto obtain dark brown residue which
  8. customwas purified by silica gel column chromatography in EtOAc-Petroleum ether
  9. customto obtain pale brown solid
  10. customThe solid was crystallized in CHCl3-petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-a596ef9e9af44004957ff473cfff879d
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722901B2

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