Phenol → HCID 66835833, compound

HRID 2404457Notes

Reaction equation

HRID 2404457 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([S:25][CH2:26][CH2:27][CH2:28][C:29]3[N:30]=[CH:31][N:32](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:33]=3)[CH:20]=2)[C:10]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[N:11]=2)[CH2:4][CH2:3]1.C1(O)C=CC=CC=1.Cl[Si](C)(C)C>ClCCCl>[N:32]1[CH:33]=[C:29]([CH2:28][CH2:27][CH2:26][S:25][C:21]2[CH:20]=[C:19]([CH:9]([O:8][CH:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)[C:10]3[NH:11][C:12]4[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=4[N:14]=3)[CH:24]=[CH:23][CH:22]=2)[NH:30][CH:31]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 6397ChlorotrimethylsilaneHCID 66835793HCID 66835793, compound

Product 1

HCID 66835833HCID 66835833, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-((1-methylpiperidin-4-yloxy){3-[3-(1-trityl-1H-imidazol-4-yl)propylsulfanyl]phenyl}methyl)-1H-benzimidazole (200 mg) in 1,2-dichloroethane (7 mL) are added phenol (270 mg) and chlorotrimethylsilane (0.37 mL). The reaction mixture is heated at reflux overnight. Volatiles are removed under reduced pressure and the residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 98/2/0.2 to 90/10/1) to give 2-[{3-[3-(3H-imidazol-4-yl)propylsulfanyl]phenyl}(1-methylpiperidin-4-yloxy)methyl]-1H-benzimidazole.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux overnight
  3. customVolatiles are removed under reduced pressure
  4. customthe residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 98/2/0.2 to 90/10/1)

Sources & evidence

ORD record
ord-8ea0b9df5f5f4cf08a15beab269cd38c
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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