Trifluoroacetic acid → 1-[1-ethyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]piperazin-2-one

HRID 1622889Notes

Reaction equation

HRID 1622889 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[CH:10][CH:11]=[C:6]2[C:5]([N:20]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][C:21]2=[O:33])=[CH:4]1)[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl.CO>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[CH:10][CH:11]=[C:6]2[C:5]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][C:21]2=[O:33])=[CH:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67818259tert-butyl 4-[1-ethyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-3-oxopiperazine-1-carboxylate

Product 1

HCID 678185661-[1-ethyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]piperazin-2-oneYield 77.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-[1-ethyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-3-oxopiperazine-1-carboxylate (4.952 g, 10.97 mmol) in DCM (20 mL) is added trifluoroacetic acid (4.15 mL, 54.84 mmol) over 2 minutes and the reaction stirred for 90 minutes. The reaction is diluted with MeOH and poured on to a SCX2 ion-exchange column. This is flushed with one column volume of MeOH, and then the product collected in the subsequent one column volume flush of 7 M methanolic ammonia. This solution is then concentrated in vacuo to give a brown oil. This is purified by column chromatography on silica, eluting with 0 to 40% MeOH in EtOAc, to give the title compound as an orange oil (2.989 g, 8.51 mmol). MS (m/z): 352 (M+1).

Workup

  1. customThis is flushed with one column volume of MeOH
  2. customthe product collected in the subsequent one column volume
  3. customflush of 7 M methanolic ammonia
  4. concentrationThis solution is then concentrated in vacuo
  5. customto give a brown oil
  6. customThis is purified by column chromatography on silica
  7. washeluting with 0 to 40% MeOH in EtOAc

Sources & evidence

ORD record
ord-0024c358ef27473ea0d1e3106d639886
Source dataset
uspto-grants-2014_07
Patent number
US08778946B2

Reaction notes

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