Methyl chloroformate → HCID 131723415, compound

HRID 861075Notes

Reaction equation

HRID 861075 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:16]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[NH:15][N:14]=2)=[CH:9][CH:8]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[OH2:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][N:15]=[C:16]([N:24]3[CH2:29][CH2:28][N:27]([C:2]([O:4][CH3:5])=[O:3])[CH2:26][CH2:25]3)[C:17]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 6586Methyl chloroformate2×HCID 178478002HCID 178478002, compound

Product 1

HCID 131723415HCID 131723415, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Methyl chloroformate (55 mg) was added to a solution of 3-(4-chlorophenyl)-4-(4-pyridyl)-5-(4-piperazinyl)pyrazole (200 mg, 0.54 mmol; prepared as set forth in Example A-169) and 4-dimethylaminopyridine (5 mg) in pyridine (10 mL). The mixture was stirred at room temperature for 3 hours. Additional methyl chloroformate (30 mg) was added and stirring was continued for 24 hours. The solvent was removed in vacuo. The residue was treated with water and extracted with ethyl acetate. After drying the organic layer (MgSO4), the solvent was blown down to a volume of 10 mL and refrigerated. The resultant crystalline solid was filtered and air dried to give 103 mg (48%) of methyl 4-[5-(4-chlorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]-1-piperazinecarboxylate, monohydrate, mp 264–265° C. Anal. Calc'd. for C20H20ClN5O2.H2O: C, 57.76; H, 5.33; N, 16.84. Found: C, 57.98; H, 4.89; N, 16.44.

Workup

  1. customprepared
  2. stirringstirring
  3. waitwas continued for 24 hours
  4. customThe solvent was removed in vacuo
  5. additionThe residue was treated with water
  6. extractionextracted with ethyl acetate
  7. dry with materialAfter drying the organic layer (MgSO4)
  8. filtrationThe resultant crystalline solid was filtered
  9. customair dried

Sources & evidence

ORD record
ord-e0bc01f6d5704d1996c0c12805aba6a7
Source dataset
uspto-grants-2006_12
Patent number
US07153959B2

Reaction notes

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