Acetyl chloride → HCID 58513616, compound

HRID 241654Notes

Reaction equation

HRID 241654 reaction equation
[Br:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]([CH2:14][CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23]C(C)(C)C)=O)[CH2:17][CH2:16]3)[C:7]([CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[N:8][C:4]=2[CH:3]=1.Cl[Si](C)(C)[CH3:32].C(N(CC)CC)C.C(Cl)(=O)C>CO.C(OCC)(=O)C>[Br:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]([CH2:14][CH:15]3[CH2:16][CH2:17][N:18]([C:21](=[O:23])[CH3:32])[CH2:19][CH2:20]3)[C:7]([CH2:9][C:10]([CH3:13])([CH3:11])[CH3:12])=[N:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 58513579HCID 58513579, compound

Product 1

HCID 58513616HCID 58513616, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-((5-bromo-2-neopentyl-1H-benzo[d]imidazol-1-yl)methyl)piperidine-1-carboxylate (STEP A, 740 mg, 1.59 mmol) in methanol (8 mL) was added chlorotrimethylsilane (4 mL). After stirring for 17 h, the mixture was concentrated in vacuo. The residue was diluted with dichloromethane (8 mL) and added triethylamine (2.24 mL, 15.9 mmol) and acetyl chloride (227 microL, 3.19 mmol). After 20 min, the mixture was diluted with ethyl acetate and washed with water, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (dichloromethane-methanol, gradient) to give the title compound (630 mg, 97%) as an amorphous.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionThe residue was diluted with dichloromethane (8 mL)
  3. waitAfter 20 min
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (dichloromethane-methanol, gradient)

Sources & evidence

ORD record
ord-e6dfaa8686fc46ce9d13b776dc5878c7
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

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