Cinnamaldehyde → HCID 178519049, compound

HRID 1404673Notes

Reaction equation

HRID 1404673 reaction equation
[CH:1](=[C:8]1/[N:9]=[C:10]([C:14]2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=2)[NH:11][C:12]/1=[O:13])/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28](=[O:37])/[CH:29]=[CH:30]/[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[CH2:30]([CH:29]1[C:28](=[O:37])[O:13][C:12]2[NH:11][C:10]([C:14]3[CH:19]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:17]=[C:16]([C:24]([F:27])([F:25])[F:26])[CH:15]=3)=[N:9][C:8]=2[CH:1]1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 637511CinnamaldehydeHCID 136341359HCID 136341359, compound

Product 1

HCID 178519049HCID 178519049, compoundYield 57%

Procedure

Prepared according to the general procedure using (Z)-4-benzylidene-2-(3,5-bis(trifluoromethyl)phenyl)-1H-imidazol-5(4H)-one and trans-cinnamaldehyde. The unpurified residue was purified by flash chromatography using 15% EtOAc/hexanes to afford 21 as an off-white solid (88 mg, 57%). Analytical data for 21: 1H NMR (500 MHz, CDCl3) δ 9.16 (s, 1H), 8.15 (s, 2H), 7.80 (s, 1H), 7.40-7.26 (m, 6H), 7.15-7.06 (m, 2H), 7.00-6.96 (m, 2H), 4.11 (d, J=6.9 Hz, 1H), 3.63 (ddd, J=10.1, 6.8, 4.6 Hz, 1H), 3.37 (dd, J=14.8, 4.7 Hz, 1H), 2.44 (dd, J=14.8, 10.1 Hz, 1H); 13C NMR (CDCl3, 126 MHz) δ 168.8, 149.4, 139.0, 137.7, 136.8, 132.4 (q, JCF=33.6 Hz), 131.2, 129.2, 129.0, 128.6, 128.4, 127.9, 126.8, 124.6 (d, JCF=4.0 Hz), 122.9 (d, JCF=273.0 Hz), 122.0, 112.1, 47.1, 38.5, 32.7; IR (film) cm−1 1780, 1641, 1618, 1528, 1401, 1361, 1279, 1186, 1133, 896, 730, 697, 682; LRMS (ESI): Mass calcd for [M+H]+ C27H19F6N2O2: 517.1. found 517.4; Enantiomeric ratio was measured by chiral phase HPLC (Chiralcel OD-H; 3% IPA/1% MeOH/hexanes 1.0 mL/min, 210 nm), Rt1 (minor)=17.2, Rt2 (major)=20.9 min; er=99:1.

Workup

  1. customPrepared
  2. customThe unpurified residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7f8f362307034209a19d4d3623954c79
Source dataset
uspto-grants-2014_12
Patent number
US08912341B2

Reaction notes

Loading…