Trifluoroacetic acid → (S)-2-(3-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)piperidin-1-yl)ethanoic acid

HRID 526875Notes

Reaction equation

HRID 526875 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])[CH2:19]4)[C:14]([F:32])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][C:25]([OH:27])=[O:26])[CH2:19]4)[C:14]([F:32])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67285705HCID 67285705, compound2×

Product 1

HCID 68007832(S)-2-(3-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)piperidin-1-yl)ethanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution tert-butyl 2-[(3S)-3-[[2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-pyrimidin-4-yl]amino]-1-piperidyl]acetate, 2b, (0.12 g, 0.26 mmol) in CH2Cl2 (4 mL) was added trifluoroacetic acid (4 mL). The reaction mixture was stirred at room temperature for 18 h and concentrated in vacuo. The crude residue was diluted with 5% MeOH/CH2Cl2 and the resulting white precipitate was filtered and washed with CH2Cl2 to afford the desired product, 577, as trifluoroacetic acid salt.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe crude residue was diluted with 5% MeOH/CH2Cl2
  3. filtrationthe resulting white precipitate was filtered
  4. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-454ff68f34b849468431e4304e18689e
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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