Trimethylsilyl isocyanate → HCID 17808983, compound

HRID 1597314Notes

Reaction equation

HRID 1597314 reaction equation
[NH2:1][C:2]1[C:23]([Cl:24])=[CH:22][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[CH2:11][CH2:10]2)=[O:7])=[C:4]([O:25][CH3:26])[CH:3]=1.C[Si]([N:31]=[C:32]=[O:33])(C)C>C(Cl)Cl>[NH2:1][C:2]1[C:23]([Cl:24])=[CH:22][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH:16]3[CH2:17][CH2:18][N:19]([C:32](=[O:33])[NH2:31])[CH2:20][CH2:21]3)[CH2:11][CH2:10]2)=[O:7])=[C:4]([O:25][CH3:26])[CH:3]=1

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 10937790HCID 10937790, compound

Product 1

HCID 17808983HCID 17808983, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-5-chloro-2-methoxy-N-[1-(4-piperidinylmethyl)-4-piperidinyl]benzamide (610 mg) in methylene chloride (30 ml) is added trimethylsilyl isocyanate (180 mg) under ice-cooling, and the mixture is stirred at room temperature for 15 hours. The reaction mixture is washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by basic silica gel column chromatography (eluent; chloroform: methanol=40:1) to give 4-amino-5-chloro-N-[1-(1-carbamoyl-4-piperidinylmethyl)-4-piperidinyl]-2-methoxybenzamide (440 mg) as white amorphous.

Workup

  1. temperaturecooling
  2. washThe reaction mixture is washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  4. customthe solvent is evaporated under reduced pressure
  5. customThe residue is purified by basic silica gel column chromatography (eluent; chloroform: methanol=40:1)

Sources & evidence

ORD record
ord-e1055962f6134a47b7b86f6b8f234d89
Source dataset
uspto-grants-2001_09
Patent number
US06294555B1

Reaction notes

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