HCID 71060717, compound → HCID 71062366, compound

HRID 528972Notes

Reaction equation

[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14]/[N:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+]([C:25]([CH2:52][CH2:53][CH2:54][CH3:55])=[CH:26][C:27]1[CH:39]=[CH:38][C:30]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[CH:29][C:28]=1[C:40]([N:42]1[CH2:51][CH2:50][C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:43]1)=[O:41])([O-])=O>>[C:34]([O:33][C:31]([C:30]1[CH:38]=[CH:39][C:27]([C:26]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:15][N:14]([C:11]3[CH:12]=[CH:13][C:8]([O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:9][CH:10]=3)[C:25]=2[CH2:52][CH2:53][CH2:54][CH3:55])=[C:28]([C:40]([N:42]2[CH2:51][CH2:50][C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[CH2:43]2)=[O:41])[CH:29]=1)=[O:32])([CH3:35])([CH3:36])[CH3:37]

Participants

Reactant 2

HCID 71060717HCID 71060717, compound

HCID 140641173HCID 140641173, compound

Product 1

HCID 71062366HCID 71062366, compoundYield 51.1%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 223E, (E)-ethyl 2-(2-(4-phenoxyphenyl)hydrazono)acetate (55 mg, 0.19 mmol) and tert-butyl 4-(2-nitrohex-1-enyl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (90 mg, 0.19 mmol) were converted to the title compound (68 mg, 50%) as a pale yellow oil. 1H NMR (CDCl3, 1:1 mixture of amide rotamers) δ 8.09 (dd, J=8, 2 Hz, 1H), 8.05-8.03 (m, 1H), 7.44-6.82 (m, 14H), 5.02-4.98 (m, 1H), 4.48-4.39 (m, 1H), 4.34-4.27 (m, 2H), 4.14-3.98 (m, 1H), 3.58-3.35 (m, 1H), 2.83-2.50 (m, 4H), 1.61 (s, 9H), 1.27 (t, J=8 Hz, 1.5H), 1.23 (t, J=8 Hz, 1.5H), 1.16-0.89 (m, 4H), 0.65-0.60 (m, 3H); MS(ESI+) m/z 700.3 (M+H)+.

Sources & evidence

ORD record: ord-3b87942b174c42d6a0b128dbfcb09f4e
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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