HCID 71060717, compound → HCID 71062298, compound

HRID 528978Notes

Reaction equation

HRID 528978 reaction equation
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][C:4]([NH:7]/[N:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:3][CH:2]=1.[N+]([C:24]([CH2:51][CH2:52][CH2:53][CH3:54])=[CH:25][C:26]1[CH:38]=[CH:37][C:29]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:28][C:27]=1[C:39]([N:41]1[CH2:50][CH2:49][C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH2:42]1)=[O:40])([O-])=O>>[C:1]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:6]=[CH:5][C:4]([N:7]2[C:24]([CH2:51][CH2:52][CH2:53][CH3:54])=[C:25]([C:26]3[CH:38]=[CH:37][C:29]([C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])=[CH:28][C:27]=3[C:39]([N:41]3[CH2:50][CH2:49][C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[CH2:42]3)=[O:40])[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:8]2)=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 71060717HCID 71060717, compoundHCID 140641169Acetic acid, 2-(2-[1,1′-biphenyl]-4-ylhydrazinylidene)-, ethyl ester, (2E)-

Product 1

HCID 71062298HCID 71062298, compoundYield 62%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 223E, (E)-ethyl 2-(2-(biphenyl-4-yl)hydrazono)acetate (35 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 (55 mg, 62%) as a pale yellow solid. 1H NMR (CDCl3, 1:1 mixture of amide rotamers) δ 8.13 (dd, J=8, 2 Hz, 1H), 8.09-8.07 (m, 1H), 7.74-7.43 (m, 10H), 7.23-6.86 (m, 4H), 5.02-4.98 (m, 1H), 4.55-4.47 (m, 1H), 4.37-4.31 (m, 2H), 4.20-4.02 (m, 1H), 3.58-3.35 (m, 1H), 2.90-2.51 (m, 4H), 1.61 (s, 9H), 1.32 (t, J=8 Hz, 1.5H), 1.26 (t, J=8 Hz, 1.5H), 1.21-0.97 (m, 4H), 0.66-0.62 (m, 3H); MS (ESI+) m/z 684.4 (M+H)+.

Sources & evidence

ORD record
ord-0901a9095c2a46f9bc2d7874ee2c8b34
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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