4-Chlorophenyl Isocyanate → HCID 68647159, compound

HRID 1162325Notes

Reaction equation

HRID 1162325 reaction equation
[NH2:1][C@H:2]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:15][C:14]3=[CH:16][N:17]=[C:18]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[N:13]3[C:12]2=[O:28])[CH2:7][CH2:6]1)=[O:4].[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([N:40]=[C:41]=[O:42])=[CH:36][CH:35]=1>C(#N)C>[Si:21]([O:20][CH2:19][C:18]1[N:13]2[C:12](=[O:28])[N:11]([CH:8]3[CH2:9][CH2:10][N:5]([C:3]([C@H:2]([NH:1][C:41]([NH:40][C:37]4[CH:38]=[CH:39][C:34]([Cl:33])=[CH:35][CH:36]=4)=[O:42])[C:29]([CH3:32])([CH3:31])[CH3:30])=[O:4])[CH2:6][CH2:7]3)[CH2:15][C:14]2=[CH:16][N:17]=1)([C:24]([CH3:25])([CH3:26])[CH3:27])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 68647776HCID 68647776, compound

Product 1

HCID 68647159HCID 68647159, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(1-((2R)-2-amino-3,3-dimethylbutanoyl)-4-piperidinyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one (0.33 g) obtained in Example 83k) in acetonitrile was added 4-chlorophenyl isocyanate (0.11 g), and then mixed at room temperature for 1 hour. Acetonitrile was distilled off under reduced pressure, and then the residue was purified with silica gel column (ethyl acetate) to obtain the title compound as a colorless solid (0.38 g, 85%).

Workup

  1. additionmixed at room temperature for 1 hour
  2. distillationAcetonitrile was distilled off under reduced pressure
  3. customthe residue was purified with silica gel column (ethyl acetate)

Sources & evidence

ORD record
ord-2fe30983f5e24db99dbadfbe9acc4783
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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