Triethylamine → HCID 66744380, Verbindung

HRID 1959454Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1959454
[C:1]([O:5][C:6]([N:8]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:9]1[C:10]([C:16]2[O:20][C:19]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][N:28]([CH3:36])[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:23][CH:22]=3)=[N:18][N:17]=2)=[N:11][C:12](Br)=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:44]1[C:48]2([CH2:52][CH2:51][NH:50][CH2:49]2)[CH2:47][N:46]([C:53](=[O:56])[CH2:54][CH3:55])[CH2:45]1.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:9]1[C:10]([C:16]2[O:20][C:19]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][N:28]([CH3:36])[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:23][CH:22]=3)=[N:18][N:17]=2)=[N:11][C:12]([N:50]2[CH2:51][CH2:52][C:48]3([CH2:44][CH2:45][N:46]([C:53](=[O:56])[CH2:54][CH3:55])[CH2:47]3)[CH2:49]2)=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 59472131HCID 59472131, VerbindungHCID 66744467HCID 66744467, Verbindung

Produkt 1

HCID 66744380HCID 66744380, VerbindungAusbeute 75,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of tert-butyl N-[[4-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-bromo-pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (153 mg, 0.23 mmol) and 1-(3,7-diazaspiro[4.4]nonan-3-yl)propan-1-one (101 mg, 0.46 mmol) in DMF (2 mL) was added Et3N (70 mg, 97 μL, 0.70 mmol). The reaction vessel was sealed and heated at 90° C. for 40 minutes. The reaction mixture was cooled to room temperature, diluted with EtOAc and washed with brine (2×). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography using 0-60% EtOAc in DCM to yield tert-butyl N-[[4-[5-[3[bis(tert-butoxycarbonyl)amino]-6-(3-propanoyl-3,7-diazaspiro[4.4]nonan-7-yl)pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (133 mg, 75%). LC/MS m/z 763.9 [M+H]+.

Aufarbeitung

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed with brine (2×)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cbc39a911d3f481084d9ae14c7a12fa6
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410112B2

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