HCID 20816145, compound → HCID 71062256, compound

HRID 528969Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]/[N:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1.[N+]([C:20]([CH2:47][CH2:48][CH2:49][CH3:50])=[CH:21][C:22]1[CH:34]=[CH:33][C:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:24][C:23]=1[C:35]([N:37]1[CH2:46][CH2:45][C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:38]1)=[O:36])([O-])=O>>[C:29]([O:28][C:26]([C:25]1[CH:33]=[CH:34][C:22]([C:21]2[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:10][N:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[C:20]=2[CH2:47][CH2:48][CH2:49][CH3:50])=[C:23]([C:35]([N:37]2[CH2:46][CH2:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH2:38]2)=[O:36])[CH:24]=1)=[O:27])([CH3:30])([CH3:31])[CH3:32]

Participants

Reactant 2

HCID 20816145HCID 20816145, compound

HCID 71060717HCID 71060717, compound

Product 1

HCID 71062256HCID 71062256, compoundYield 45%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 223E, (E)-ethyl 2-(2-(4-methoxyphenyl)hydrazono)acetate (24 mg, 0.108 mmol) and tert-butyl 4-(2-nitrohex-1-enyl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (50 mg, 0.108 mmol) were converted to the title compound (31 mg, 45%) as a colorless oil. 1H NMR (CDCl3, 1:1 mixture of amide rotamers) δ 8.08 (dd, J=8, 2 Hz, 1H), 8.03-8.02 (m, 1H), 7.42-6.81 (m, 9H), 5.02-4.98 (m, 1H), 4.46-4.38 (m, 1H), 4.32-4.26 (m, 2H), 4.15-3.98 (m, 1H), 3.86 (s, 1.5H), 3.85 (s, 1.5H), 3.54-3.33 (m, 1H), 2.81-2.45 (m, 4H), 1.61 (s, 9H), 1.28 (t, J=8 Hz, 1.5H), 1.22 (t, J=8 Hz, 1.5H), 1.30-0.95 (m, 4H), 0.61-0.57 (m, 3H); MS(ESI+) m/z 638.3 (M+H)+.

Sources & evidence

ORD record: ord-cf2f031450c541988be387a7c5c1d09c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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