Dimethylformamide → HCID 9931002, compound

HRID 1838264Notes

Reaction equation

HRID 1838264 reaction equation
[CH3:1][CH:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1.F[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:11]([O:10][C:8]([N:4]1[CH2:5][CH2:6][N:7]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:28])([F:30])[F:29])[CH:20]=2)[CH:2]([CH3:1])[CH2:3]1)=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 6050854-Fluoro-2-(trifluoromethyl)benzonitrileHCID 104215421-Cbz-3-Methylpiperazine

Product 1

HCID 9931002HCID 9931002, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 1.01 g portion of benzyl 3-methylpiperazine-1-carboxylate synthesized in Reference Example 10, 814 mg of 4-fluoro-2-trifluoromethylbenzonitrile and 2.38 g of potassium carbonate were added to 20 ml of DMF and stirred at 100° C. for 20 hours. This was mixed with water, extracted with ethyl acetate and dried, and then the solvent was evaporated. The resulting residue was purified by a silica gel column chromatography to obtain 440 mg of the title compound from ethyl acetate-hexane (3:1, v/v) eluate.

Workup

  1. extractionextracted with ethyl acetate
  2. customdried
  3. customthe solvent was evaporated
  4. customThe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-bf903aea420249fbb9ed052228d24de2
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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