Trifluoroacetic acid → HCID 77981870, compound

HRID 716069Notes

Reaction equation

HRID 716069 reaction equation
[C:1]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([CH:23]=[C:24]([N:27]4[CH:31]=[N:30][CH:29]=[N:28]4)[C:25]#[N:26])=[CH:19][CH:18]=3)[N:14]=2)[N:9](COCC[Si](C)(C)C)[CH:8]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C(O)(C(F)(F)F)=O.O.O.O.C([O-])(=O)C.[Na+]>C(Cl)Cl.C(O)C>[C:1]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([CH:23]=[C:24]([N:27]4[CH:31]=[N:30][CH:29]=[N:28]4)[C:25]#[N:26])=[CH:19][CH:18]=3)[N:14]=2)[NH:9][CH:8]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 23665404Sodium Acetate TrihydrateHCID 71015365HCID 71015365, compound

Product 1

HCID 77981870HCID 77981870, compoundYield 5.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a 25 ml one necked round bottom flask, 3-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)-2-(1H-1,2,4-triazol-1-yl)acrylonitrile (0.052 g, 0.95 mmole) was taken in CH2Cl2 (5 mL). TFA (1.5 mL) was added drop wise at 0° C. After completion of the addition, the reaction mass was warmed up to RT and stirred for 16 hrs at the same temperature. After completion of the reaction, CH2Cl2 was distilled out to get solid. The solid was taken in ethanol (10 mL) and sodium acetate trihydrate (0.130 g, 0.95 mmole) was added at RT. The reaction mixture was stirred for 20 hrs at RT. After completion of the reaction the ethanol was distilled out under vacuum. To the residue, water (20 mL) was added and stirred for 15 min, filtered and wash with water and n-pentane. The solid was dried under vacuum to yield 21 mg of 3-(4-(7-pivaloyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)-2-(1H-1,2,4-triazol-1-yl)acrylonitrile.

Workup

  1. additionAfter completion of the addition
  2. customthe reaction
  3. distillationwas distilled out
  4. customto get solid
  5. stirringThe reaction mixture was stirred for 20 hrs at RT
  6. distillationwas distilled out under vacuum
  7. additionTo the residue, water (20 mL) was added
  8. stirringstirred for 15 min
  9. filtrationfiltered
  10. washwash with water and n-pentane
  11. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-b95d16e187a74d9380a01f1c7eb8b602
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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