Phenol → HCID 66835833, compound

HRID 572867Notes

Reaction equation

HRID 572867 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-a2c89f63a80d4d039e1c0a401b9c4e87
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

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