HCID 71060717, compound → HCID 86718922, compound

HRID 528977Notes

Reaction equation

[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11]/[N:12]=[CH:13]/[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[N+]([C:22]([CH2:49][CH2:50][CH2:51][CH3:52])=[CH:23][C:24]1[CH:36]=[CH:35][C:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:26][C:25]=1[C:37]([N:39]1[CH2:48][CH2:47][C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH2:40]1)=[O:38])([O-])=O>>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:22]([CH2:49][CH2:50][CH2:51][CH3:52])=[C:23]([C:24]3[CH:36]=[CH:35][C:27]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])=[CH:26][C:25]=3[C:37]([N:39]3[CH2:48][CH2:47][C:46]4[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=4)[CH2:40]3)=[O:38])[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:12]2)=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

Reactant 2

HCID 71060717HCID 71060717, compound

HCID 140641171HCID 140641171, compound

Product 1

HCID 86718922HCID 86718922, compoundYield 67%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 223E, (E)-ethyl 2-(2-(4-(allyloxy)phenyl)hydrazono)acetate (64 mg, 0.26 mmol) and tert-butyl 4-(2-nitrohex-1-enyl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (120 mg, 0.26 mmol) were converted to the title compound (114 mg, 67%) as a pale yellow oil. 1H NMR (CDCl3, 1:1 mixture of amide rotamers) δ 8.10 (dd, J=8, 2 Hz, 1H), 8.04-8.03 (m, 1H), 7.43-6.81 (m, 9H), 6.11-6.04 (m, 1H), 5.45-5.40 (m, 1H), 5.34-5.30 (m, 1H), 5.02-4.98 (m, 1H), 4.59-4.57 (m, 2H), 4.48-4.38 (m, 1H), 4.32-4.26 (m, 2H), 4.15-3.98 (m, 1H), 3.58-3.32 (m, 1H), 2.86-2.45 (m, 4H), 1.61 (s, 9H), 1.27 (t, J=8 Hz, 1.5H), 1.20 (t, J=8 Hz, 1.5H), 1.11-0.92 (m, 4H), 0.62-0.57 (m, 3H); MS(ESI+) m/z 664.4 (M+H)+.

Sources & evidence

ORD record: ord-99c838c178064d4193463c4201eb4121
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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