Lithium iodide → HCID 178489052, compound

HRID 2174103Notes

Reaction equation

HRID 2174103 reaction equation
[C:1]([C:3]1[CH:30]=[CH:29][C:6]2[NH:7][C:8]([C:10]3([C:17]4[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH3:28])=[C:22]5[C:18]=4[CH:19]=[CH:20][NH:21]5)[CH2:12][CH:11]3[C:13]([O:15]C)=[O:14])=[N:9][C:5]=2[CH:4]=1)#[N:2].[I-].[Li+]>N1C=CC=CC=1>[C:1]([C:3]1[CH:30]=[CH:29][C:6]2[NH:7][C:8]([C:10]3([C:17]4[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH3:28])=[C:22]5[C:18]=4[CH:19]=[CH:20][NH:21]5)[CH2:12][CH:11]3[C:13]([OH:15])=[O:14])=[N:9][C:5]=2[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 178496867HCID 178496867, compound

Product 1

HCID 178489052HCID 178489052, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of (±)-methyl 2-(5-cyano-1H-benzo[d]imidazol-2-yl)-2-(5-methoxy-7-methyl-1H-indol-4-yl)cyclopropanecarboxylate (Example 142-C) (40 mg, 0.1 mmol) in pyridine (5.0 mL) was added lithium iodide (800 mg, 59.8 mmol) and this mixture was stirred at 125° C. overnight. The reaction was partitioned between EtOAc and cold 0.5N HCl solution and the layers separated. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by RP-HPLC (HC-B) to give the title compound. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.75 (br.s., 1H), 7.55 (br.s., 1H) 7.27-7.55 (m, 1H) 7.17 (br.s., 1H) 6.79 (s, 1H) 6.50 (d, J=3.03 Hz, 1H) 3.81 (s, 3H) 2.52 (s, 3H) 2.22 (d, J=7.33 Hz, 1H) 1.30 (t, J=6.57 Hz, 1H), 0.88-0.92 (m, 1H). HRMS calcd. for C22H18N4O3 (M+H)+ 387.1412. found 387.1443.

Workup

  1. customThe reaction was partitioned between EtOAc and cold 0.5N HCl solution
  2. customthe layers separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by RP-HPLC (HC-B)

Sources & evidence

ORD record
ord-c502257342834ec7bed2de93711bf74c
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

Loading…