HCID 11768643, compound → HCID 178519053, compound

HRID 1404669Notes

Reaction equation

HRID 1404669 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]1(/[CH:28]=[CH:29]/[CH:30]=[O:31])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH:22]1([CH2:28][CH:29]2[C:30](=[O:31])[O:13][C:12]3[NH:11][C:10]([C:14]4[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=4[F:21])=[N:9][C:8]=3[CH:1]2[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 11768643HCID 11768643, compoundHCID 136341358(Z)-4-benzylidene-2-(2,5-difluorophenyl)-1H-imidazol-5(4H)-one

Product 1

HCID 178519053HCID 178519053, compoundYield 56%

Procedure

Prepared according to the general procedure using (Z)-4-benzylidene-2-(2,5-difluorophenyl)-1H-imidazol-5(4H)-one and (E)-3-cyclohexylacrylaldehyde. After 72 h, the reaction only reached 64% conversion by 1H NMR. The unpurified residue was purified by flash chromatography using 15% EtOAc/hexanes to afford 19 as an off-white solid (71 mg, 56%). Analytical data for 19: 1H NMR (500 MHz, CDCl3) δ 9.45 (d, J=8.3 Hz, 1H), 7.90 (ddd, J=9.2, 6.1, 3.2 Hz, 1H), 7.36-7.27 (m, 3H), 7.13-7.04 (m, 3H), 7.01-6.93 (m, 1H), 4.24 (d, J=6.9 Hz, 1H), 3.29 (q, J=6.9 Hz, 1H), 1.74-1.61 (m, 6H), 1.49-1.40 (m, 1H), 1.29-1.18 (m, 2H), 1.18-1.04 (m, 2H), 0.91-0.81 (m, 2H); 13C NMR (CDCl3, 126 MHz) δ 169.5, 159.1 (d, JCF=243.4 Hz), 155.4 (dd, JCF=240.8, 2.1 Hz), 149.3, 137.3, 136.3, 129.2, 128.1, 127.7, 118.5 (dd, JCF=12.9, 9.1 Hz), 117.1 (dd, JCF=25.7, 8.7 Hz), 116.5 (dd, JCF=24.7, 9.5 Hz), 114.5 (dd, JCF=27.0, 3.8 Hz), 110.6 (d, JCF=3.9 Hz), 43.0, 39.6, 34.6, 34.4, 33.4, 32.8, 26.4, 26.2, 26.1; IR (film) cm−1 2923, 2851, 1770, 1637, 1619, 1529, 1481, 1463, 1450, 1387, 1172, 1115, 1094, 881, 812, 766, 737, 700; LRMS (ESI): Mass calcd for [M+H]+ C25H25F2N2O2: 423.2. found 423.4; Enantiomeric ratio was measured by chiral phase HPLC (Chiralcel OD-H; 15% IPA/hexanes 0.7 mL/min, 280 nm), Rt1 (major)=9.1, Rt2 (minor)=25.0 min; er=98:2.

Workup

  1. customPrepared
  2. customthe reaction only reached 64% conversion by 1H NMR
  3. customThe unpurified residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6fd34d9160c140dba2e41e0472a1a0a5
Source dataset
uspto-grants-2014_12
Patent number
US08912341B2

Reaction notes

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