Trifluoroacetic acid → HCID 9888317, compound

HRID 1838267Notes

Reaction equation

HRID 1838267 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C@@H:21]([CH3:22])[CH2:20][N:19]([C:23]([NH:25][C:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH:32]C(OC(C)(C)C)=O)[N:27]=3)=[O:24])[C@H:18]([CH3:40])[CH2:17]2)=[CH:12][C:11]=1[C:41]([F:44])([F:43])[F:42])#[N:9]>ClC(Cl)C>[NH2:32][C:28]1[N:27]=[C:26]([NH:25][C:23]([N:19]2[CH2:20][C@H:21]([CH3:22])[N:16]([C:13]3[CH:14]=[CH:15][C:10]([C:8]#[N:9])=[C:11]([C:41]([F:44])([F:43])[F:42])[CH:12]=3)[CH2:17][C@H:18]2[CH3:40])=[O:24])[CH:31]=[CH:30][N:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20610860HCID 20610860, compound

Product 1

HCID 9888317HCID 9888317, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A 15 ml portion of trifluoroacetic acid was added to 60 ml of dichloroethane solution containing 2.8 g of (2R,5S)-4-(4-cyano-3-trifluoromethylphenyl)-N-[2-(1,1-dimethylethoxycarbonyl)amino-4-pyrimidyl]-2,5-dimethylpiperazine-1-carboxamide synthesized in Example 6-2, and the mixture was stirred at room temperature for about 12 hours. The reaction solution was evaporated under reduced pressure, and the thus obtained residue was mixed with saturated sodium bicarbonate solution and extracted with chloroform. The thus obtained organic layer was washed with water and dried over anhydrous magnesium sulfate, and then the crude product obtained by evaporating the solvent was subjected to a silica gel column chromatography to obtain 1.97 g of the title compound from chloroform-methanol (30:1, v/v) eluate. Thereafter, this was crystallized from ethyl acetate-hexane to obtain 1.51 g of the title compound as crystals.

Workup

  1. customThe reaction solution was evaporated under reduced pressure
  2. additionthe thus obtained residue was mixed with saturated sodium bicarbonate solution
  3. extractionextracted with chloroform
  4. washThe thus obtained organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe crude product obtained
  7. customby evaporating the solvent

Sources & evidence

ORD record
ord-a610b805643e42da9057947fae051545
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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