Trifluoroacetic acid → 2-(4-methylpiperazine-1-carbonyl)-3-(4-(7-pivaloyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)acrylonitrile

HRID 716038Notes

Reaction equation

HRID 716038 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10](=[CH:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[N:22]=[C:23]4[C:29]([C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:28][N:27](COCC[Si](C)(C)C)[C:24]4=[N:25][CH:26]=3)=[CH:16][CH:15]=2)[C:11]#[N:12])=[O:9])[CH2:4][CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]([C:10](=[CH:13][C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]3[N:22]=[C:23]4[C:29]([C:30](=[O:35])[C:31]([CH3:33])([CH3:32])[CH3:34])=[CH:28][NH:27][C:24]4=[N:25][CH:26]=3)=[CH:18][CH:19]=2)[C:11]#[N:12])=[O:9])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 710144592-(4-methylpiperazine-1-carbonyl)-3-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)acrylonitrile

Product 1

HCID 710141882-(4-methylpiperazine-1-carbonyl)-3-(4-(7-pivaloyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)acrylonitrileYield 36.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 35 ml vial, 2-(4-methylpiperazine-1-carbonyl)-3-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)acrylonitrile (0.100 g, 0.0001 mole) was taken in CH2Cl2 (8 ml) and cooled to 0° C. under N2 atm. TFA (2 ml, 0.0238 mole) was added drop wise at 0° C. and stirred for 16 h at room temperature. After completion of the reaction, the solvent was evaporated under reduced pressure from the reaction mixture and saturated NaHCO3 solution was added dropwise to make pH basic. The solid which precipitated out was filtered and washed with water and pentane. The solid (0.050 g) was taken in ethanol (20 ml), NaOAc.3H2O (0.226 g, 0.0016 mole) was added and the reaction mixture and stirred at room temperature for 32 hr. Ethanol was evaporated under reduced pressure from the reaction mixture and obtained solid material was washed with water and pentane. The crude compound was purified by triturating with pentane to yield 0.017 g of 2-(4-methylpiperazine-1-carbonyl)-3-(4-(7-pivaloyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)acrylonitrile.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated under reduced pressure from the reaction mixture and saturated NaHCO3 solution
  3. additionwas added dropwise
  4. customThe solid which precipitated out
  5. filtrationwas filtered
  6. washwashed with water and pentane
  7. stirringthe reaction mixture and stirred at room temperature for 32 hr
  8. customEthanol was evaporated under reduced pressure from the reaction mixture
  9. customobtained solid material
  10. washwas washed with water and pentane
  11. customThe crude compound was purified
  12. customby triturating with pentane

Sources & evidence

ORD record
ord-181b7cb2baaa4126881e1a30ca4dba63
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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