Trifluoroacetic acid → Diethylbenzamide

HRID 735581노트

반응식

HRID 735581 반응식
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]

참가 물질

4

반응물 3

HCID 6422Trifluoroacetic acidHCID 2724699PyBOPHCID 579563642-(4-(2-(3-(Aminomethyl)phenylcarbamoyloxy)ethyl)-3-methylphenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acid

생성물 1

HCID 17906983Diethylbenzamide수율 42%

실험 절차

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)+.

후처리

  1. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-cbd79f67000b4c49b84c37b06be2185b
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592331B2

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