Trifluoroacetic acid → Diethylbenzamide

反応式

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]

参加物

反応物 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

生成物 1

HCID 17906983Diethylbenzamide収率 42%

実験手順

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)+.

後処理

custompurified by reverse phase HPLC

出典と根拠

ORDレコード: ord-cbd79f67000b4c49b84c37b06be2185b
出典データセット: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07592331B2

反応ノート

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