Trifluoroacetic acid → (r)-2-Amino-1-(4-(5-bromo-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-2-cyclohexylethanone

HRID 79522Notes

Reaction equation

HRID 79522 reaction equation
[Br:1][C:2]1[C:3]([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:33])[C@H:18]([NH:25]C(=O)OC(C)(C)C)[CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:13][CH2:12]2)=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C(Cl)Cl>[NH2:25][C@H:18]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[C:17]([N:14]1[CH2:15][CH2:16][N:11]([C:3]2[C:2]([Br:1])=[CH:7][N:6]=[C:5]3[NH:8][CH:9]=[CH:10][C:4]=23)[CH2:12][CH2:13]1)=[O:33]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 68758555(R)-tert-Butyl 2-(4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-1-cyclohexyl-2-oxoethylcarbamate

Product 1

HCID 44198752(r)-2-Amino-1-(4-(5-bromo-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-2-cyclohexylethanoneYield 62.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-tert-Butyl 2-(4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-1-cyclohexyl-2-oxoethylcarbamate (0.010 g, 0.019 mmol) was placed in DCM (3 mL) at room temperature. TFA (0.3 mL) was then added. The reaction was stirred at room temperature for 1 hour. The reaction was then concentrated to dryness, dissolved in minimal DCM, and added dropwise to a stirring solution of 1M HCl in ether. The solid product was filtered, washed with ether, and dried to give (R)-2-amino-1-(4-(5-bromo-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)-2-cyclohexylethanone (0.005 g, 62% yield) as the dihydrochloride salt. MS ESI (+) m/z 421 detected.

Workup

  1. concentrationThe reaction was then concentrated to dryness
  2. dissolutiondissolved in minimal DCM
  3. additionadded dropwise to a stirring solution of 1M HCl in ether
  4. filtrationThe solid product was filtered
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-f4f16e6457164f6688e4c6f5ef7da4b7
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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