Hydrochloric Acid → HCID 69000968, Verbindung

HRID 735874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 735874
[CH2:1]([O:3][C:4](=[O:35])[C:5]([N:7]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32](O)=[O:33])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=[O:6])[CH3:2].C1C=CC2N(O)N=NC=2C=1.[CH2:46]([NH2:54])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53].Cl>C(Cl)Cl.C(Cl)CCl>[CH2:1]([O:3][C:4](=[O:35])[C:5]([N:7]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([NH:54][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])=[O:33])=[CH:28][CH:27]=2)=[CH:24][CH:25]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:17])([F:16])[F:18])=[CH:11][CH:10]=1)=[O:6])[CH3:2]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8143OctylamineHCID 757711-HydroxybenzotriazoleHCID 67185822HCID 67185822, Verbindung

Produkt 1

HCID 69000968HCID 69000968, VerbindungAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 4′-({[ethoxy(oxo)acetyl][4-(trifluoromethyl)benzyl]amino}methyl)-1,1′-biphenyl-4-carboxylic acid (100 mg), EDC (47 mg) and HOBt (28 mg) in DCM (4 mL) was added octylamine (0.041 mL). The resulting reaction mixture was stirred for 3 h. DCM (15 mL) and an aqueous solution of HCl (1N, 10 mL) was added. The aqueous layer was extracted with DCM (3×15 mL). The combined organic layers were washed with a saturated solution of NaHCO3 (15 mL) and dried over MgSO4. Evaporation of the solvents gave an oil which was purified by flash chromatography over silica gel (c-Hex/AcOEt 2/1) to give the title compound as a colorless oil (41 mg, 33%). M+(LC/MS(ESI)): 597.8; M−(LC/MS(ESI)): 595.0. HPLC (Condition A), Rt: 6.61 min (HPLC purity: 99.87%)

Aufarbeitung

  1. customThe resulting reaction mixture
  2. extractionThe aqueous layer was extracted with DCM (3×15 mL)
  3. washThe combined organic layers were washed with a saturated solution of NaHCO3 (15 mL)
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvents
  6. customgave an oil which
  7. customwas purified by flash chromatography over silica gel (c-Hex/AcOEt 2/1)

Quellen und Nachweise

ORD-Eintrag
ord-88e9b70cf36a4109b6aa282f2075c5ac
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592477B2

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