Hydrochloric Acid → 2-(2,4-Dioxo-5-phenyl-3-methyl-3-phenylcarbamoylmethyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl acetamide

HRID 343191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 343191
C(C(C1C=CC=CC=1)(C(=O)N)[N:5]1C(=O)C(CC(O)=O)(C)C(=O)N(C2C=CC=CC=2)[C:7]2[CH:25]=[CH:26][CH:27]=[CH:28][C:6]1=2)(C)C.C([O:45][C:46]([CH2:48][C:49]1([CH2:83]C(O)=O)[C:55](=[O:56])[N:54]([C:57](C(C)C)(C2C=CC(OC)=CC=2)[C:58](=[O:60])[NH2:59])[C:53]2[CH:72]=[CH:73][CH:74]=[CH:75][C:52]=2[N:51]([C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)[C:50]1=[O:82])=O)C1C=CC=CC=1.N[C:88]1[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=1.[CH2:94]1[CH2:98]N([P+](Br)(N2CCCC2)N2CCCC2)C[CH2:95]1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.Cl>CN(C=O)C>[O:56]=[C:55]1[N:54]([CH2:57][C:58]([N:59]([CH:94]([CH3:98])[CH3:95])[C:88]2[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=2)=[O:60])[C:53]2[CH:72]=[CH:73][CH:74]=[CH:75][C:52]=2[N:51]([C:76]2[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=2)[C:50](=[O:82])[C:49]1([CH3:83])[CH2:48][C:46](=[O:45])[NH:5][C:6]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:7]=1

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 67696769[1-(isopropyl-phenyl-carbamoylmethyl)-3-methyl-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]acetic acidHCID 86753587{3-(Benzyloxycarbonyl-methyl)-1-[isopropyl-(4-methoxy-phenyl)-carbamoylmethyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl}acetic acid

Produkt 1

HCID 100310132-(2,4-Dioxo-5-phenyl-3-methyl-3-phenylcarbamoylmethyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 35 mg (0.07 mmol) of [1-(isopropyl-phenyl-carbamoylmethyl)-3-methyl-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]acetic acid, prepared as in Intermediate 7, 0.013 mL (0.14 mmol) of aniline, 66 mg (0.14 mmol) of PyBrOP and 0.05 mL (0.23 mmol) of N,N-diisopropyl-N-ethylamine in 2 mL of DMF is stirred at RT for 2 d. The reaction mixture is diluted with 30 mL of 1N HCl and extracted with EtOAc (×3). The organic extract is washed with 1N HCl, brine, sat. NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo to a yellow oil. Purification by reverse phase C-18 MPLC (70% methanol/TFA-H2O) gave 16 mg of the title compound as a white powder; m.p. 228°-9° C.; 1H NMR (d6 -DMSO 300 MHz, mixture of conformations) δ9.73 (s, 1H), 7.6-7.2 (m, 16H), 7.05 (m, 2H), 6.65 (d, 1H, J=8), 4.85 (m, 1H), 4.22 (m, 2H), 2.33 (m, 2H), 1.20 (s, 3H), 1.00 (m, 6H); low resolution MS (FAB) m/e 575 (MH+).

Aufarbeitung

  1. extractionextracted with EtOAc (×3)
  2. extractionThe organic extract
  3. washis washed with 1N HCl, brine, sat. NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo to a yellow oil
  6. customPurification by reverse phase C-18 MPLC (70% methanol/TFA-H2O)

Quellen und Nachweise

ORD-Eintrag
ord-a71892a7589b4e19a57ae429ef76c23e
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859007

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