Triethylamine → 5-(alpha-Hydroxy-alpha-2-pyridylbenzyl)-N-[2'-(4''-methoxycinnamamido)ethyl]-7-(alpha-2-pyridylbenzylidene)-5-norbornene-2,3-dicarboximide

HRID 1496800Notes

Reaction equation

HRID 1496800 reaction equation
[OH:1][C:2]([C:15]1[CH:16]2[C:21](=[C:22](C3C=CC=CN=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:19]([CH:20]=1)[CH:18]1[C:35]([N:37]([CH2:40]COC(=O)C=CC3C=CC(C(C)C)=CC=3)[C:38](=[O:39])[CH:17]21)=[O:36])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:56][O:57][C:58]1[CH:68]=[CH:67][C:61]([CH:62]=[CH:63][C:64]([OH:66])=O)=[CH:60][CH:59]=1.[CH2:69]([N:71]=C=NCCCN(C)C)C.C(N(CC)CC)C.CN([C:90]1[CH:95]=[CH:94][CH:93]=[CH:92][N:91]=1)C>ClCCl>[OH:1][C:2]([C:15]1[CH:16]2[C:21](=[C:22]([C:90]3[CH:95]=[CH:94][CH:93]=[CH:92][N:91]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:19]([CH:20]=1)[CH:18]1[C:35]([N:37]([CH2:40][CH2:69][NH:71][C:64](=[O:66])[CH:63]=[CH:62][C:61]3[CH:60]=[CH:59][C:58]([O:57][CH3:56])=[CH:68][CH:67]=3)[C:38](=[O:39])[CH:17]21)=[O:36])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 132454-Methoxy cinnamic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 1178180985-(alpha-Hydroxy-alpha-2-pyridylbenzyl)-N-[2'-(4''-isopropylcinnamoyloxy)ethyl]-7-(alpha-2-pyridyl benzylidene)-5-norbornene-2,3-dicarboximide

Product 1

HCID 1178180915-(alpha-Hydroxy-alpha-2-pyridylbenzyl)-N-[2'-(4''-methoxycinnamamido)ethyl]-7-(alpha-2-pyridylbenzylidene)-5-norbornene-2,3-dicarboximideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A similar procedure (Schwartz, E. et al. Macromolecules 2011, 44, 4735-4741) to that previously described for the preparation of 347 was followed using 106 (0.8 g, 0.7 mmol), 4-methoxycinnamic acid (0.1 g, 0.8 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.16 g, 0.8 mmol), triethylamine (0.1 mL, 0.8 mmol) and dimethylaminopyridine (9 mg, 0.07 mmol) in dichloromethane (10 mL), at room temperature for 24 h. Purification by flash chromatography (hexane/ethyl acetate 1:5) afforded 361 as a white solid (0.4 g, 0.6 mmol, 85%). 1H NMR (300 MHz, CDCl3) δ 3.35-3.91 (6.6H, m, NCH2CH2NHCO, H-2, H-3, U/H-1, V/H-1, W/H-4), 3.83-3.85 (3H, m, OMe), 3.95 (0.4H, m, Y/H-4), 4.15 (0.1H, m, U/H-4), 4.33 (0.3H, m, V/H-4), 4.47-4.50 (0.6H, m, W/H-1, Y/H-1), 5.46 (0.6H, s, OH), 5.53 (0.3H, dd, m, V/H-6), 5.56 (0.4H, m, Y/H-6), 5.77 (0.4, s, OH), 6.20-6.40 (1.3H, m, COCH═CH, W/H-6, U/H-6), 6.70-7.65 (21H, m, Ar and COCH═CH), 8.40-8.62 (2H, m, αPyr).

Workup

  1. customPurification by flash chromatography (hexane/ethyl acetate 1:5)

Sources & evidence

ORD record
ord-915388f0770243f0a3af5cf02ec1b141
Source dataset
uspto-grants-2015_12
Patent number
US09198420B2

Reaction notes

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