Trifluoroacetic acid → HCID 44199125, compound

HRID 79568Notes

Reaction equation

HRID 79568 reaction equation
[O:1]=[C:2]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:23][N:22]=[C:21]3[NH:31][CH:32]=[CH:33][C:20]=23)[CH2:15][CH2:14]1)[CH2:3][CH2:4][NH:5]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:5][CH2:4][CH2:3][C:2]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:23][N:22]=[C:21]3[NH:31][CH:32]=[CH:33][C:20]=23)[CH2:15][CH2:14]1)=[O:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68761488HCID 68761488, compound

Product 1

HCID 44199125HCID 44199125, compoundYield 119.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-oxo-3-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)propylcarbamate (0.054 g, 0.12 mmol) was placed in DCM (3 mL) at room temperature. TFA (0.3 mL) was added, and the reaction was stirred at room temperature for 1 hour. The reaction was then concentrated to dryness. The resulting residue was dissolved in minimal DCM and added to a stirring solution of 1M HCl in ether. The resulting solid was collected by filtration, washed with ether, and dried to give 3-amino-1-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-one (0.050 g, 99% yield). MS ESI (+) m/z 350 detected.

Workup

  1. concentrationThe reaction was then concentrated to dryness
  2. dissolutionThe resulting residue was dissolved in minimal DCM
  3. additionadded to a stirring solution of 1M HCl in ether
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-f88623b5903a4ea1940605b23bd88d85
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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