(S)-pentan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate → HCID 178448289, Verbindung

HRID 245752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 245752
Br[C:2]1[N:3]=[C:4]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][N:19]([CH3:21])[CH3:20])[CH2:14][CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=12.[CH3:22][O:23][C:24]1[CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH:27]=[CH:26][C:25]=1[NH:39][C:40](=[O:47])[O:41][C@H:42]([CH2:44][CH2:45][CH3:46])[CH3:43]>>[CH3:20][N:19]([CH2:18][C@H:15]1[CH2:16][CH2:17][C@H:12]([C:4]2[N:5]3[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]3=[C:2]([C:28]3[CH:27]=[CH:26][C:25]([NH:39][C:40](=[O:47])[O:41][C@H:42]([CH2:44][CH2:45][CH3:46])[CH3:43])=[C:24]([O:23][CH3:22])[CH:29]=3)[N:3]=2)[CH2:13][CH2:14]1)[CH3:21]

Komponenten

3

Edukt 2

HCID 67364014(S)-pentan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamateHCID 178432908HCID 178432908, Verbindung

Produkt 1

HCID 178448289HCID 178448289, VerbindungAusbeute 24 %

Versuchsvorschrift

1-((Trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)-N,N-dimethylmethanamine (26 mg) and (S)-pentan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (27 mg) were used according to the procedure described in example 4 step 4c and the crude product was purified by prep-HPLC (column Luna C18(2); gradient acetonitrile/water with constant 0.003M trifluoroacetic acid). Proper fractions were collected and made basic with aqueous sodium hydrogencarbonate, extracted with dichloromethane, organic layer dried (Na2SO4) and concentrated in vacuo to give (S)-pentan-2-yl 4-(3-((trans)-4-((dimethylamino)methyl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate (9 mg).

Aufarbeitung

  1. customthe crude product was purified by prep-HPLC (column Luna C18(2); gradient acetonitrile/water with constant 0.003M trifluoroacetic acid)
  2. customProper fractions were collected
  3. extractionextracted with dichloromethane, organic layer
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-340ec7241c9b45638b9e35c6f72ec851
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658794B2

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