Trimethylsilyl isocyanate → HCID 59510503, compound

HRID 602288Notes

Reaction equation

HRID 602288 reaction equation
[NH2:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5]([C:6]([NH:8][CH2:9][CH:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH2:11]2)=[O:7])=[C:4]([O:26][CH2:27][CH3:28])[CH:3]=1.C[Si]([N:33]=[C:34]=[O:35])(C)C>C(Cl)Cl>[NH2:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5]([C:6]([NH:8][CH2:9][CH:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][CH:17]3[CH2:18][CH2:19][N:20]([C:34](=[O:35])[NH2:33])[CH2:21][CH2:22]3)[CH2:11]2)=[O:7])=[C:4]([O:26][CH2:27][CH3:28])[CH:3]=1

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 59510469HCID 59510469, compound

Product 1

HCID 59510503HCID 59510503, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-5-chloro-2-ethoxy-N-[{4-(4-piperidinylmethyl)-2-morpholinyl}-methyl]benzamide (Example 22) (1.0 g) in methylene chloride (15 ml) was added trimethylsilyl isocyanate (0.34 g) at room temperature, and the mixture was stirred for 2.5 hours. The solvent was removed in vacuo, and then to the residue was added water. The precipitated solid was filtered in vacuo, washed with aqueous ethanol and dried to give the titled compound (1.0 g) as a white solid. Melting point 201-207° C. (recrystallized from E/H)

Workup

  1. customThe solvent was removed in vacuo
  2. additionto the residue was added water
  3. filtrationThe precipitated solid was filtered in vacuo
  4. washwashed with aqueous ethanol
  5. customdried

Sources & evidence

ORD record
ord-567808c382094621a7003400aee6ff69
Source dataset
uspto-grants-2011_03
Patent number
US07906510B2

Reaction notes

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