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Diisopropylethylamine → HCID 178520723, Verbindung

HRID 2378988
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2378988
[Br:1][C:2]1[C:10]2[C:9]3[CH2:11][N:12]([CH2:21][C:22]([F:25])([F:24])[F:23])[C:13](=[O:20])[C@H:14]([CH2:16][C:17]([OH:19])=O)[CH2:15][C:8]=3[CH:7]=[C:6]([Br:26])[C:5]=2[NH:4][N:3]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH:58]1[CH2:63][CH2:62][CH:61]([N:64]2[CH2:70][CH2:69][C:68]3[CH:71]=[CH:72][CH:73]=[CH:74][C:67]=3[NH:66][C:65]2=[O:75])[CH2:60][CH2:59]1>CN(C)C=O>[Br:1][C:2]1[C:10]2[C:9]3[CH2:11][N:12]([CH2:21][C:22]([F:25])([F:24])[F:23])[C:13](=[O:20])[C@H:14]([CH2:16][C:17](=[O:19])[N:58]4[CH2:59][CH2:60][CH:61]([N:64]5[CH2:70][CH2:69][C:68]6[CH:71]=[CH:72][CH:73]=[CH:74][C:67]=6[NH:66][C:65]5=[O:75])[CH2:62][CH2:63]4)[CH2:15][C:8]=3[CH:7]=[C:6]([Br:26])[C:5]=2[NH:4][N:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 178525536HCID 178525536, Verbindung

Produkt 1

HCID 178520723HCID 178520723, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(S)-2-(1,4-Dibromo-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino [3,4-e]indazol-7-yl)acetic acid (52 mg, 0.104 mmol) was dissolved in N,N-dimethylformamide (1.5 mL). N,N-Diisopropylethylamine (70 μl, 0.402 mmol) was added to the mixture followed by TBTU (34.8 mg, 0.108 mmol). 3-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one (35.4 mg, 0.144 mmol) was then added to the mixture. Reaction stirred at room temperature for 1 hour. Reaction was quenched with 50% acetonitrile-water. Material was purified by reverse phase prep HPLC (acetonitrile-water-trifluoroacetic acid). Acetonitrile was removed from the fractions by roto-vap. Remaining aqueous was made basic with aqueous sodium bicarbonate. Material was extracted twice with ethyl acetate. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as white solid in 67% yield. 1H NMR (500 MHz, DMSO-D6) δ ppm 13.92 (s, 1H) 8.51 (s, 1H) 7.48 (s, 1H) 6.98-7.08 (m, 3H) 6.76-6.86 (m, 1H) 5.58 (d, J=17.40 Hz, 1H) 5.39 (d, J=17.09 Hz, 1H) 4.49 (d, J=13.12 Hz, 1H) 4.26-4.42 (m, 2H) 4.10-4.24 (m, 1H) 3.90-4.09 (m, 2H) 3.33-3.41 (m, 2H) 3.19 (d, J=16.79 Hz, 1H) 3.05-3.15 (m, 1 H) 2.95-3.02 (m, 1H) 2.83-2.94 (m, 3H) 2.53-2.65 (m, 1H) 2.33-2.46 (m, 1H) 1.58-1.85 (m, 3H) 1.40-1.57 (m, 1H). High resolution MS m/e (M+H)+=725.0720.

Aufarbeitung

  1. customReaction
  2. customReaction
  3. customwas quenched with 50% acetonitrile-water
  4. customMaterial was purified by reverse phase prep HPLC (acetonitrile-water-trifluoroacetic acid)
  5. customAcetonitrile was removed from the fractions by roto-vap
  6. extractionMaterial was extracted twice with ethyl acetate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-c3dfb384f4e541028815100b758a5f83
Quelldatensatz
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07470680B2

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