Dimethylformamide → HCID 23150566, Verbindung

HRID 228035

Reaktionsgleichung

Reaktionsgleichung von HRID 228035
O[N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2N=N1.[CH2:11]([O:18][C:19](C12CCC(C(O)=O)(CC1)CC2)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl.CN(C)CCCN=C=N[CH2:41][CH3:42].Cl.[F:45][C:46]1([F:53])[CH2:51][CH2:50][CH:49]([NH2:52])[CH2:48][CH2:47]1.CN(C)[CH:56]=[O:57]>C(N(CC)CC)C>[CH2:11]([O:18][C:19]([NH:2][C:6]12[CH2:42][CH2:41][C:9]([C:56]([NH:52][CH:49]3[CH2:50][CH2:51][C:46]([F:53])([F:45])[CH2:47][CH2:48]3)=[O:57])([CH2:8][CH2:7]1)[CH2:10][CH2:5]2)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

7

Edukt 5

HCID 6228Dimethylformamide2×HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23150613HCID 23150613, VerbindungHCID 231506694,4-Difluorocyclohexan-1-amine hydrochloride

Produkt 1

HCID 23150566HCID 23150566, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

1-Hydroxybenzotriazole (138 mg), 4-benzyloxycarbonylbicyclo[2.2.2]octane-1-carboxylic acid (72.0 mg) and N,N-dimethylformamide (8 mL) were mixed together. While the mixture was chilled in an ice bath, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (265 mg) was added and the mixture was stirred at room temperature for 1 hour. Subsequently, a mixture of 4,4-difluorocyclohexylamine hydrochloride (108 mg), triethylamine (105 μL) and N,N-dimethylformamide (2 mL) was added and the resultant mixture was stirred at room temperature for 18 hours and was then concentrated under reduced pressure. Water (10 mL) was added to the residue and the solution was extracted with ethyl acetate (3×10 mL). The ethyl acetate extracts were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by a silica gel column (eluant:hexane:ethyl acetate=3:1) to give 4-benzyloxycarbonylamino-N-(4,4-difluorocyclohexyl)bicyclo[2.2.2]octane-1-carboxamide (57.0 mg) as a white solid.

Aufarbeitung

  1. temperatureWhile the mixture was chilled in an ice bath
  2. additionwas added
  3. concentrationwas then concentrated under reduced pressure
  4. additionWater (10 mL) was added to the residue
  5. extractionthe solution was extracted with ethyl acetate (3×10 mL)
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by a silica gel column (eluant:hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-31c91e7700664c3c8f91c6486ccfa022
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560569B2

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