Dimethylamine → HCID 67411120, Verbindung

HRID 1715581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1715581
CS(OS(C)(=O)=O)(=O)=O.[C:10]([C:14]1[CH:15]=[C:16]([NH:20][C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[NH:31][C:32]2[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=2)[N:37]([CH2:41][CH2:42][CH2:43]O)[N:36]=[CH:35]3)=[O:22])[N:17]([CH3:19])[N:18]=1)([CH3:13])([CH3:12])[CH3:11].[CH:45]([N:48](C(C)C)[CH2:49]C)(C)C.CNC>C1COCC1>[C:10]([C:14]1[CH:15]=[C:16]([NH:20][C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[NH:31][C:32]2[CH:40]=[C:39]3[C:38](=[CH:34][CH:33]=2)[N:37]([CH2:41][CH2:42][CH2:43][N:48]([CH3:49])[CH3:45])[N:36]=[CH:35]3)=[O:22])[N:17]([CH3:19])[N:18]=1)([CH3:11])([CH3:12])[CH3:13]

Komponenten

6

Edukt 4

HCID 674Dimethylamine2×HCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 67409607HCID 67409607, Verbindung

Produkt 1

HCID 67411120HCID 67411120, VerbindungAusbeute 43,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methanesulfonic anhydride (12 mg, 0.070 mmol) was added to a solution of alcohol (7s) (24 mg, 0.050 mmol) and diisopropylethylamine (20 mg, 0.15 mmol) at room temperature. The solution was stirred for 1 hour. Dimethylamine (2.0 M in THF, 0.25 mL, 0.50 mmol) was added and the reaction was stirred overnight. Additional dimethylamine was added (2.0 M in THF, 0.25 mL, 0.50 mmol) and the reaction was stirred an additional 2 days. The mixture was then partitioned between CHCl3 and water. The aqueous phase was extracted once with CHCl3. The organic phases were combined, dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified on silica gel with 5% MeOH/CH2Cl2 containing 1% Et3N to provide the desired compound (8s-1) (11 mg, 43% yield) as a dark foam. 1H NMR (400 MHz, CDCl3) δ 7.81 (s, 1H), 7.42 (s, 1H), 7.35-7.33 (m, 2H), 7.19-7.11 (m, 4H), 6.80-6.75 (m, 2H), 5.94 (s, 1H), 5.55 (m, 1H), 4.43 (d, J=6.6 Hz, 2H), 4.38 (t, J=10.5 Hz, 2H), 3.57 (s, 3H), 2.24 (t, J=10.5 Hz, 2H), 2.19 (s, 6H), 2.08-2.01 (m, 2H), 1.24 (s, 9H); MS (ESI+) m/z 503 (M+H)+; HPLC (5 to 95%) 2.59 min.

Aufarbeitung

  1. stirringthe reaction was stirred overnight
  2. stirringthe reaction was stirred an additional 2 days
  3. customThe mixture was then partitioned between CHCl3 and water
  4. extractionThe aqueous phase was extracted once with CHCl3
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified on silica gel with 5% MeOH/CH2Cl2 containing 1% Et3N

Quellen und Nachweise

ORD-Eintrag
ord-9d512d72500b47fab485ec8422ee1cde
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799782B2

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