Trifluoroacetic acid → HCID 86662057, compound

HRID 869262Notes

Reaction equation

HRID 869262 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)=[C:18]([O:29][CH3:30])[CH:17]=2)[C:5]([C:12]([NH2:14])=[O:13])=[N:6][C:7]=1[C:8](O)([CH3:10])[CH3:9].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[Cl:1][C:2]1[N:3]=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)=[C:18]([O:29][CH3:30])[CH:17]=2)[C:5]([C:12]([NH2:14])=[O:13])=[N:6][C:7]=1[CH:8]([CH3:10])[CH3:9]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86662058HCID 86662058, compound

Product 1

HCID 86662057HCID 86662057, compoundYield 75.8%

Procedure

To a mixture of 5-chloro-6-(2-hydroxypropan-2-yl)-3-{[3-methoxy-4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide (Preparation Example 544) (300 mg) and trifluoroacetic acid (3 mL), triethylsilane (0.55 mL) was added under ice cooling and stirred under ice cooling for 10 minutes and at room temperature for 22 hours. After the reaction liquid was concentrated, the residue was diluted with chloroform and washed with saturated aqueous sodium hydrogen carbonate. After drying over anhydrous magnesium sulfate, the solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent; chloroform:methanol:saturated aqueous ammonia=100:0:0 to 20:1:0.1) to give a crude product. The crude product was washed with diisopropyl ether to give 5-chloro-6-isopropyl-3-{[3-methoxy-4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide (219 mg) as an orange solid.

Workup

  1. additionwas added under ice cooling
  2. customAfter the reaction liquid
  3. concentrationwas concentrated
  4. additionthe residue was diluted with chloroform
  5. washwashed with saturated aqueous sodium hydrogen carbonate
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customthe residue was purified by silica gel column chromatography (eluent; chloroform:methanol:saturated aqueous ammonia=100:0:0 to 20:1:0.1)
  9. customto give a crude product
  10. washThe crude product was washed with diisopropyl ether

Sources & evidence

ORD record
ord-c2a35a34fb1b491e87c421a790ddb99e
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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