HCID 71060717, compound → HCID 71062333, compound

HRID 528976Notes

Reaction equation

[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10]/[N:11]=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:5]=1.[N+]([C:21]([CH2:48][CH2:49][CH2:50][CH3:51])=[CH:22][C:23]1[CH:35]=[CH:34][C:26]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:25][C:24]=1[C:36]([N:38]1[CH2:47][CH2:46][C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39]1)=[O:37])([O-])=O>>[C:30]([O:29][C:27]([C:26]1[CH:34]=[CH:35][C:23]([C:22]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:11][N:10]([C:7]3[CH:6]=[CH:5][C:4]([CH2:3][CH2:2][OH:1])=[CH:9][CH:8]=3)[C:21]=2[CH2:48][CH2:49][CH2:50][CH3:51])=[C:24]([C:36]([N:38]2[CH2:47][CH2:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH2:39]2)=[O:37])[CH:25]=1)=[O:28])([CH3:31])([CH3:32])[CH3:33]

Participants

Reactant 2

HCID 71060717HCID 71060717, compound

HCID 140641164HCID 140641164, compound

Product 1

HCID 71062333HCID 71062333, compoundYield 17.1%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 223E, (E)-ethyl 2-(2-(4-(2-hydroxyethyl)phenyl)hydrazono)acetate (61 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 (29 mg, 17%) as a pale yellow oil. 1H NMR (CDCl3, 1:1 mixture of amide rotamers) δ 8.10 (dd, J=8, 2 Hz, 1H), 8.05-8.03 (m, 1H), 7.44-6.82 (m, 9H), 5.02-4.98 (m, 1H), 4.48-4.38 (m, 1H), 4.32-4.26 (m, 2H), 4.15-3.98 (m, 1H), 3.89-3.88 (m, 2H), 3.58-3.38 (m, 1H), 2.96-2.92 (m, 2H), 2.88-2.50 (m, 4H), 1.61 (s, 9H), 1.29 (t, J=8 Hz, 1.5H), 1.21 (t, J=8 Hz, 1.5H), 1.13-0.95 (m, 4H), 0.62-0.57 (m, 3H); MS(ESI+) m/z 652.3 (M+H)+.

Sources & evidence

ORD record: ord-9c718f5b50d54ba782bc90aa6bad2ea7
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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