HCID 20400411, compound → HCID 72208441, compound

HRID 2174521Notes

Reaction equation

[C:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][NH2:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:19]([O:21]C1C=C2C(=CC=1)NC(C)=C2C=O)C>>[C:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][NH2:18])=[CH:14][CH:15]=2)[C:10]([CH:19]=[O:21])=[CH:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

Reactant 2

HCID 20400411HCID 20400411, compound

HCID 34178155HCID 34178155, compound

Product 1

HCID 72208441HCID 72208441, compoundYield 73%

Procedure

This compound was prepared from 416 (297 mg, 1.21 mmol) in a manner similar to that for 409a to yield a cream-colored solid (243 mg, 73%): mp 126-128° C. TLC Rf 0.50 (80% EtOAc/hexanes). 1H NMR (600 MHz, d6-DMSO) δ 12.10 (s, 1H), 9.91 (s, 1H), 8.27 (m, 1H), 8.00 (s, 1H), 7.45-7.43 (m, 2H), 7.17-7.15 (d, 1H, J=8.4 Hz), 4.22-4.20 (d, 2H, J=6 Hz), 1.40 (s, 9H). 13C NMR (150 MHz, CDCl3) δ 184.7, 155.7, 138.6, 136.0, 134.0, 124.0, 123.1, 119.2, 118.0, 112.0, 77.6, 43.7, 28.2. Elemental analysis calculated for C15H18N2O3: C, 65.68; H, 6.61; N, 10.21. Found: C, 65.75; H, 6.61; N, 10.20.

Sources & evidence

ORD record: ord-094cd5c526d94c608bea41123cf2b9a6
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09061994B1

Reaction notes

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