HCID 71060717, compound → HCID 71062360, compound

HRID 528975Notes

Reaction equation

[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12]/[N:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[N+]([C:23]([CH2:50][CH2:51][CH2:52][CH3:53])=[CH:24][C:25]1[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:27][C:26]=1[C:38]([N:40]1[CH2:49][CH2:48][C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:41]1)=[O:39])([O-])=O>>[C:32]([O:31][C:29]([C:28]1[CH:36]=[CH:37][C:25]([C:24]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][N:12]([C:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:7][CH:8]=3)[C:23]=2[CH2:50][CH2:51][CH2:52][CH3:53])=[C:26]([C:38]([N:40]2[CH2:49][CH2:48][C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH2:41]2)=[O:39])[CH:27]=1)=[O:30])([CH3:33])([CH3:34])[CH3:35]

Participants

Reactant 2

HCID 71060717HCID 71060717, compound

HCID 140641175HCID 140641175, compound

Product 1

HCID 71062360HCID 71062360, compoundYield 69.7%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 223E, (E)-ethyl 2-(2-(4-butoxyphenyl)hydrazono)acetate (51 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 (90 mg, 68%) as a pale yellow oil. 1H NMR (CDCl3, 1:1 mixture of amide rotamers) δ 8.11 (dd, J=8, 2 Hz, 1H), 8.07-8.05 (m, 1H), 7.46-6.88 (m, 9H), 5.02-4.98 (m, 1H), 4.48-4.38 (m, 1H), 4.33-4.28 (m, 2H), 4.18-3.98 (m, 3H), 3.58-3.32 (m, 1H), 2.85-2.50 (m, 4H), 1.85-1.79 (m, 2H), 1.61 (s, 9H), 1.59-1.51 (m, 2H), 1.31 (t, J=8 Hz, 1.5H), 1.23 (t, J=8 Hz, 1.5H), 1.13-0.95 (m, 7H), 0.65-0.60 (m, 3H); MS(ESI+) m/z 680.3 (M+H)+.

Sources & evidence

ORD record: ord-9d472f806ac7451b989d4c2ea7cd41df
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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