HCID 71060717, compound → HCID 71062171, compound

HRID 528973Notes

Reaction equation

[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13]/[N:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[N+]([C:26]([CH2:53][CH2:54][CH2:55][CH3:56])=[CH:27][C:28]1[CH:40]=[CH:39][C:31]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:30][C:29]=1[C:41]([N:43]1[CH2:52][CH2:51][C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH2:44]1)=[O:42])([O-])=O>>[C:35]([O:34][C:32]([C:31]1[CH:39]=[CH:40][C:28]([C:27]2[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:14][N:13]([C:10]3[CH:9]=[CH:8][C:7]([O:6][C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:22][CH:21]=4)=[CH:12][CH:11]=3)[C:26]=2[CH2:53][CH2:54][CH2:55][CH3:56])=[C:29]([C:41]([N:43]2[CH2:52][CH2:51][C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH2:44]2)=[O:42])[CH:30]=1)=[O:33])([CH3:36])([CH3:37])[CH3:38]

Participants

Reactant 2

HCID 71060717HCID 71060717, compound

HCID 140641167HCID 140641167, compound

Product 1

HCID 71062171HCID 71062171, compoundYield 46.1%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 223E, (E)-ethyl 2-(2-(4-(4-chlorophenoxy)phenyl)hydrazono)acetate (41 mg, 0.13 mmol) and tert-butyl 4-(2-nitrohex-1-enyl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (60 mg, 0.13 mmol) were converted to the title compound (44 mg, 46%) as a pale yellow oil. 1H NMR (CDCl3, 1:1 mixture of amide rotamers) δ 8.09 (dd, J=8, 2 Hz, 1H), 8.04-8.03 (m, 1H), 7.43-6.81 (m, 13H), 5.02-4.98 (m, 1H), 4.48-4.38 (m, 1H), 4.33-4.27 (m, 2H), 4.18-3.98 (m, 1H), 3.58-3.32 (m, 1H), 2.85-2.48 (m, 4H), 1.61 (s, 9H), 1.28 (t, J=8 Hz, 1.5H), 1.20 (t, J=8 Hz, 1.5H), 1.15-0.91 (m, 4H), 0.63-0.59 (m, 3H); MS(ESI+) m/z 734.2 (M+H)+.

Sources & evidence

ORD record: ord-c0eee8fee51d4b91b5434d935fa9c2c7
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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