1-Methylpiperazine → 4-[4-ethoxy-3-(trifluoromethyl)phenyl]-7-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

HRID 522292Notes

Reaction equation

HRID 522292 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.C(C(=NO[C+](N(C)C)N1CCOCC1)C(OCC)=O)#N.[C:44]([C:46]1[N:47]=[C:48]([C:59]2[CH:64]=[CH:63][C:62]([O:65][CH2:66][CH3:67])=[C:61]([C:68]([F:71])([F:70])[F:69])[CH:60]=2)[C:49]2[CH:54]=[CH:53][N:52]([CH2:55][C:56](O)=[O:57])[C:50]=2[N:51]=1)#[N:45]>O.CN(C=O)C>[CH2:66]([O:65][C:62]1[CH:63]=[CH:64][C:59]([C:48]2[C:49]3[CH:54]=[CH:53][N:52]([CH2:55][C:56]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[O:57])[C:50]=3[N:51]=[C:46]([C:44]#[N:45])[N:47]=2)=[CH:60][C:61]=1[C:68]([F:69])([F:70])[F:71])[CH3:67]

Participants

7

Reactant 4

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 90065599{2-cyano-4-[4-ethoxy-3-(trifluoromethyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}acetic acidHCID 178472143HCID 178472143, compound

Product 1

HCID 1178995474-[4-ethoxy-3-(trifluoromethyl)phenyl]-7-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Methylpiperazine (42 μL), N,N-diisopropylethylamine (66 μL), and (1-cyano-2-ethoxy-2-oxoethylidene aminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate (187 mg) were added to a mixture of {2-cyano-4-[4-ethoxy-3-(trifluoromethyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}acetic acid (100 mg) and DMF (4 mL) at room temperature, and the mixture was stirred at the same temperature for 2 hours. After water was added to the reaction mixture, the precipitate was collected by filtration, and washed with water. After the obtained solid was dissolved in CHCl3, the solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3:MeOH=100:0 to 50:50), whereby 4-[4-ethoxy-3-(trifluoromethyl)phenyl]-7-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (82 mg) was obtained as a white solid.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with water
  3. dissolutionAfter the obtained solid was dissolved in CHCl3
  4. concentrationthe solution was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (CHCl3:MeOH=100:0 to 50:50)

Sources & evidence

ORD record
ord-9fea9a1a8cb64d1797ceb0c09108ed39
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

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