Trifluoroacetic acid → Diethylbenzamide

HRID 735581Notes

Reaction equation

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]

Participants

Reactant 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

Product 1

HCID 17906983DiethylbenzamideYield 42%

Procedure

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)+.

Workup

custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-cbd79f67000b4c49b84c37b06be2185b
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592331B2

Reaction notes

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