HCID 13721206, compound → HCID 71062589, compound

HRID 528968Notes

Reaction equation

[C:1]1([NH:7]/[N:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+]([C:18]([CH3:45])=[CH:19][C:20]1[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:22][C:21]=1[C:33]([N:35]1[CH2:44][CH2:43][C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:36]1)=[O:34])([O-])=O>>[C:27]([O:26][C:24]([C:23]1[CH:31]=[CH:32][C:20]([C:19]2[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:8][N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:18]=2[CH3:45])=[C:21]([C:33]([N:35]2[CH2:44][CH2:43][C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:36]2)=[O:34])[CH:22]=1)=[O:25])([CH3:28])([CH3:29])[CH3:30]

Participants

Reactant 2

HCID 13721206HCID 13721206, compound

HCID 77998863HCID 77998863, compound

Product 1

HCID 71062589HCID 71062589, compoundYield 67.5%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 224E, (E)-ethyl 2-(2-phenylhydrazono)acetate (22 mg, 0.11 mmol) and tert-butyl 4-(2-nitroprop-1-enyl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (48 mg, 0.11 mmol) were converted to the title compound (42 mg, 65%) as a colorless oil. 1H NMR (CDCl3, 1:1 mixture of amide rotamers) δ 8.10 (dd, J=8, 2 Hz, 1H), 8.06-8.04 (m, 1H), 7.49-7.40 (m, 6H), 7.21-6.81 (m, 4H), 5.02-4.96 (m, 1H), 4.49-4.28 (m, 3H), 4.17-4.03 (m, 1H), 3.54-3.33 (m, 1H), 2.82-2.43 (m, 2H), 2.19 (s, 3H), 1.61 (s, 9H), 1.28 (t, J=8 Hz, 1.5H), 1.23 (t, J=8 Hz, 1.5H); MS(ESI+) m/z 566.3 (M+H)+.

Sources & evidence

ORD record: ord-ec284c96e35e461fb27b4cd4803d4294
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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