Dichloromethane → HCID 178482257, Verbindung

HRID 1189672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1189672
[F:1][C:2]([F:30])([F:29])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:28])[C:11]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[C:14]([NH:20][CH3:21])=[CH:13][C:12]=2[N:22]([CH3:27])[CH2:23][C:24]([NH2:26])=O)[CH2:5][CH2:4]1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.C(Cl)Cl.C1COCC1>C([O-])(O)=O.[Na+]>[F:1][C:2]([F:29])([F:30])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:28])[C:11]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[C:14]([NH:20][CH3:21])=[CH:13][C:12]=2[N:22]([CH3:27])[CH2:23][C:24]#[N:26])[CH2:5][CH2:4]1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 178482258HCID 178482258, Verbindung

Produkt 1

HCID 178482257HCID 178482257, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A mixture of N-(trans-4-trifluoromethyl-cyclohexyl)-2-[N-methyl-N-aminocarbonylmethyl-amino]-4-methylamino-5-nitro-benzoic acid amide (compound IIIa, 45 mg, 0.104 mmol), Burgess reagent (27 mg, 0.11 mmol, +20 mg after 0.5 h, +15 mg after 2.5 h, +20 mg after 16 h), DCM (2 mL) and THF (2 mL) is stirred for 2.5 h at rt, then for 13.5 h at 40° C. and then for 2 h at reflux. The mixture is diluted with sat aq NaHCO3, extracted with EtOAc and the combined organic phases are dried with Na2SO4, filtered and concentrated and directly used in the next step. Yield: 80 mg. HPLC Rt=1.36 min (method A). MS m/z: 414 [M+H]+.

Aufarbeitung

  1. waitfor 13.5 h at 40° C.
  2. temperaturefor 2 h at reflux
  3. extractionextracted with EtOAc
  4. dry with materialthe combined organic phases are dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a8762f9aa2fc4f048fdc6c1917a8854a
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674113B2

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