Trichloroacetyl isocyanate → (R)-(4-(4-(4-benzoyl-2-methylpiperazin-1-yl)phthalazin-1-yl)phenyl)methyl carbamate

HRID 1689979Notes

Reaction equation

HRID 1689979 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([N:19]3[CH2:24][CH2:23][N:22]([C:25]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:26])[CH2:21][C@H:20]3[CH3:33])=[N:11][N:10]=2)=[CH:5][CH:4]=1.ClC(Cl)(Cl)[C:36]([N:38]=C=O)=[O:37]>C(Cl)(Cl)Cl>[C:36](=[O:37])([O:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([N:19]3[CH2:24][CH2:23][N:22]([C:25](=[O:26])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:21][C@H:20]3[CH3:33])=[N:11][N:10]=2)=[CH:5][CH:4]=1)[NH2:38]

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 46891248(R)-(4-(4-(4-(hydroxymethyl)phenyl)phthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanone

Product 1

HCID 57581509(R)-(4-(4-(4-benzoyl-2-methylpiperazin-1-yl)phthalazin-1-yl)phenyl)methyl carbamate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Compound 81 was prepared as described in general Method K. (R)-(4-(4-(4-(hydroxymethyl)phenyl)phthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanone (JK-28) (125 mg, 0.285 mmol), was dissolved in chloroform (2.50 mL). 2,2,2-trichloroacetyl isocyanate (40.5 μl, 0.342 mmol) was added and the reaction stirred at rt for 80 minutes. The reaction was adsorbed onto alumina (Brockmann II, 3 g), and after 2 hours was eluted with 10% methanol in dichloromethane. The resulting solution was evaporated to give a yellow oil. Chromatography over silica gel with a gradient of hexanes/0-45% ethyl acetate gave a pale yellow solid, compound 81. MS (M+H)+=482.2

Workup

  1. customCompound 81 was prepared
  2. washafter 2 hours was eluted with 10% methanol in dichloromethane
  3. customThe resulting solution was evaporated
  4. customto give a yellow oil

Sources & evidence

ORD record
ord-2e2aae027fb24322b497bcf44d8f32f5
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

Loading…