2-(3,5-Dimethylpyrazolyl)-4,5-dihydroimidazole hydrobromide → HCID 86600673, compound

HRID 23995Notes

Reaction equation

HRID 23995 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][CH:6]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH2:23][CH2:24][O:25][NH2:26])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].Br.CC1C([C:35]2[NH:36][CH2:37][CH2:38][N:39]=2)=C(C)NN=1>CO>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][CH:6]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH2:23][CH2:24][O:25][NH:26][C:35]3[NH:39][CH2:38][CH2:37][N:36]=3)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 534351342-(3,5-Dimethylpyrazolyl)-4,5-dihydroimidazole hydrobromideHCID 66819270HCID 66819270, compound

Product 1

HCID 86600673HCID 86600673, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[5-(2-aminooxy-ethoxy)-indol-1yl]-3-phenyl-propionic acid ethyl ester (208 mg, 0.56 mmol) and 2-(3,5-dimethylpyrazolyl)-4,5-dihydroimidazole hydrobromide (125 mg, 0.90 mmol) were dissolved in methanol (3 mL) and stirred for 5 days. The solvent was evaporated under vacuum and the crude mixture was purified via column chromatography with silica gel, eluting with 10% methanol in dichloromethane to afford the title compound (99% yield). 1H NMR (CDCl3) δ 7.16-7.29 (m, 7H), 7.07 (d, 1H, J=2.3 Hz), 6.80 (dd, 1H, J=2.3, 8.8 Hz), 6.47 (d, 1H, J=3.2 Hz), 6.00 (t, 1H, J=7.0 Hz), 4.24 (m, 2H), 4.17 (m, 2H), 4.03 (c, 2H, J=7.2 Hz), 3.51 (br s, 4H), 3.26 (m, 2H), 1.09 (t, 3H, J=7.2 Hz).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe crude mixture was purified via column chromatography with silica gel
  3. washeluting with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-2b73fb15214441c2aee04cb641dbecbd
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

Loading…