Acrolein → HCID 178431799, compound

HRID 1404670Notes

Reaction equation

HRID 1404670 reaction equation
[CH:1](=[C:8]1/[N:9]=[C:10]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])[NH:11][C:12]/1=[O:13])/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:22]([CH:24]=[CH2:25])=[O:23]>>[F:21][C:15]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=1[C:10]1[NH:11][C:12]2[O:13][C:22](=[O:23])[CH:24]([CH3:25])[CH:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:8]=2[N:9]=1

Participants

3

Reactant 2

HCID 7847AcroleinHCID 136341358(Z)-4-benzylidene-2-(2,5-difluorophenyl)-1H-imidazol-5(4H)-one

Product 1

HCID 178431799HCID 178431799, compoundYield 42%

Procedure

Prepared according to the general procedure using (Z)-4-benzylidene-2-(2,5-difluorophenyl)-1H-imidazol-5(4H)-one and acrolein. After 72 h, the reaction only reached 63% conversion by 1H NMR. The unpurified residue was purified by flash chromatography using 15% EtOAc/hexanes to afford 20 as an off-white solid (43 mg, 42%). Analytical data for 20: 1H NMR (500 MHz, CDCl3) δ 9.48 (br s, 1H), 7.91 (ddd, J=9.2, 6.1, 3.2 Hz, 1H), 7.37-7.27 (m, 3H), 7.12-7.03 (m, 3H), 7.02-6.95 (m, 1H), 4.21 (d, J=7.2 Hz, 1H), 3.36 (ap, J=7.0 Hz, 1H), 1.11 (d, J=6.9 Hz, 3H); 13C NMR (CDCl3, 126 MHz) δ 169.6, 159.1 (d, JCF=243.9 Hz), 155.4 (dd, JCF=241.1, 2.5 Hz), 149.5, 137.0, 136.5, 129.2, 128.2, 127.8, 118.5 (dd, JCF=12.6, 9.0 Hz), 117.1 (dd, JCF=25.6, 8.7 Hz), 116.6 (dd, JCF=24.8, 9.4 Hz), 114.5 (dd, JCF−1 26.9, 3.9 Hz), 110.1 (d, JCF=3.7 Hz), 41.1, 40.7, 13.4; IR (film) cm−1 3083, 3029, 2987, 1773, 1758, 1636, 1618, 1529, 1482, 1464, 1411, 1236, 1173, 1132, 1084, 1062, 919, 873, 813, 766, 737, 700; LRMS (ESI): Mass calcd for [M+H]+ C19H15F2N2O2: 341.1. found 341.3; Enantiomeric ratio was measured by chiral phase HPLC (Chiralcel OD-H; 12% IPA/hexanes 1.0 mL/min, 280 nm), Rt1 (major)=14.4, Rt2 (minor)=27.6 min; er=>99:1.

Workup

  1. customPrepared
  2. customthe reaction only reached 63% conversion by 1H NMR
  3. customThe unpurified residue was purified by flash chromatography

Sources & evidence

ORD record
ord-77e982f0509b4a62b448f79607c6e007
Source dataset
uspto-grants-2014_12
Patent number
US08912341B2

Reaction notes

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