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1,2-Dichloroethane → HCID 59403524, Verbindung

HRID 1514209
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1514209
[CH3:1][CH:2]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[C:14]([F:17])([F:16])[F:15])[CH3:3].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.O[NH:33][C:34](=[NH:53])[C:35]1[CH:52]=[CH:51][C:38]2[CH2:39][CH2:40][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:42][CH2:43][C:37]=2[CH:36]=1>CN(C=O)C>[CH3:3][CH:2]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]2[O:11][N:33]=[C:34]([C:35]3[CH:52]=[CH:51][C:38]4[CH2:39][CH2:40][N:41]([C:44]([O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:45])[CH2:42][CH2:43][C:37]=4[CH:36]=3)[N:53]=2)=[CH:7][C:6]=1[C:14]([F:17])([F:16])[F:15])[CH3:1]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 225977674-Isopropoxy-3-(trifluoromethyl)benzoic acidHCID 178451593HCID 178451593, Verbindung

Produkt 1

HCID 59403524HCID 59403524, VerbindungAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

4-[(1-Methylethyl)oxy]-3-(trifluoromethyl)benzoic acid (Preparation 39) (744 mg, 3.00 mmol), HOBT (446 mg, 3.30 mmol) and EDC (630 mg, 3.30 mmol) were stirred in DMF (28 ml) under argon for 20 minutes. 1,1-dimethylethyl 7-[(hydroxyamino)(imino)methyl]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (Preparation 41) (915 mg, 3.00 mmol) was added and the mixture stirred at room temperature for 2 hrs before it was heated to 80° C. for 20 hrs. The reaction mixture was partitioned between EtOAc and water and the organic layer washed with aqueous sodium bicarbonate before it was dried in the usual manner and evaporated. The residue was purified by Biotage Horizon, reverse phase cartridge, eluting with 5-100% acetonitrile in water to give the title compound (749 mg, 1.45 mmol). δH (d6DMSO, 400 MHz): 8.40 (1H, dd), 8.31 (1H, d), 7.89 (1H, br.s), 7.86 (1H, dd), 7.58 (1H, d), 7.37 (1H, d), 4.98 (1H, septet), 3.54-3.46 (4H, m), 3.00-2.92 (4H, m), 1.41 (9H, s), 1.36 (6H, d).

Aufarbeitung

  1. temperaturewas heated to 80° C. for 20 hrs
  2. customThe reaction mixture was partitioned between EtOAc and water
  3. washthe organic layer washed with aqueous sodium bicarbonate before it
  4. customwas dried in the usual manner
  5. customevaporated
  6. customThe residue was purified by Biotage Horizon, reverse phase cartridge
  7. washeluting with 5-100% acetonitrile in water

Quellen und Nachweise

ORD-Eintrag
ord-ac1416c43bd84b90b39414c6caf126ae
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08222245B2

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