Trifluoroacetic acid → Diethylbenzamide

HRID 735581Notizen

Reaktionsgleichung

NCC1C=C(NC(OCCC2C=CC(C(N[C:26]3[CH:27]=[C:28]4[C:33](=[CH:34][CH:35]=3)[C:32]([N:36](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=N[CH:30]=[CH:29]4)C(O)=O)=CC=2C)=O)C=CC=1.[CH2:52]1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)C[CH2:53]1.F[P-](F)(F)(F)(F)F.C(O)(C(F)(F)F)=[O:86]>>[CH2:52]([C:27]1[C:28]([CH2:29][CH3:30])=[C:33]([CH:34]=[CH:35][CH:26]=1)[C:32]([NH2:36])=[O:86])[CH3:53]

Komponenten

Edukt 3

HCID 6422Trifluoroacetic acid

HCID 2724699PyBOP

HCID 579563642-(4-(2-(3-(Aminomethyl)phenylcarbamoyloxy)ethyl)-3-methylphenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acid

Produkt 1

HCID 17906983DiethylbenzamideAusbeute 42 %

Versuchsvorschrift

Using a procedure analogous to that used to prepare Example 28, 30F (140 mg, 0.2 mmol) was cyclized with PyBOP instead of BOP, deprotected with TFA, and purified by reverse phase HPLC to give Example 30 (40 mg, 42%) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 2.32 (s, 1.5 H) 2.48 (s, 1.5 H) 2.70-2.88 (m, 1 H) 3.04-3.22 (m, 1 H) 3.88-4.23 (m, 2 H) 4.41-4.61 (m, 1 H) 4.64-4.80 (m, 1 H) 5.09-5.17 (m, J=3.54 Hz, 1 H) 6.09-6.26 (m, J=12.13 Hz, 1 H) 6.61-6.72 (m, 2 H) 6.72-6.83 (m, J=12.88, 7.07 Hz, 1 H) 6.83-6.94 (m, J=7.58 Hz, 1 H) 7.03-7.20 (m, 3 H) 7.21-7.33 (m, 2 H) 7.36-7.54 (m, 1 H) 7.98-8.10 (m, J=9.09, 5.05 Hz, 1 H) 8.50-8.70 (m, 1 H), mixture of two atropisomers. MS (ESI) m/z 482.20 (M+H)+.

Aufarbeitung

custompurified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag: ord-cbd79f67000b4c49b84c37b06be2185b
Quelldatensatz: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07592331B2

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