Trifluoroacetic acid → 1,4-Bis-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-piperazin-2-one

HRID 1433006Notes

Reaction equation

HRID 1433006 reaction equation
C(OC([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH:10]=[C:9]1[CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[N:33](C(OC(C)(C)C)=O)[C:32]3[CH:31]=[CH:30][N:29]=[CH:28][C:27]=3[CH:26]=2)[CH2:20][C:19]1=[O:41])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH:10]=[C:9]1[CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[NH:33][C:32]3[CH:31]=[CH:30][N:29]=[CH:28][C:27]=3[CH:26]=2)[CH2:20][C:19]1=[O:41]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 690284622-[4-(1-tert-Butoxycarbonyl-1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-2-oxo-piperazin-1-ylmethyl]-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 540885701,4-Bis-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-piperazin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 2-[4-(1-tert-Butoxycarbonyl-1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-2-oxo-piperazin-1-ylmethyl]-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (85 mg, 0.14 mmol) in CH2Cl2 (5 mL) is added TFA (1 mL) at 0° C. and the solution is allowed to slowly warm to ambient temperature. After 16 h, the reaction mixture is concentrated to dryness, diluted with water and purified by reverse-phase HPLC [Buffer A: water w/0.1% TFA; Buffer B: CH3CN w/0.1% TFA; Gradient: 0% B to 45% B over 30 min] to provide 35 mg (36%, two steps) of the title compound as a pale yellow, lyophilized solid.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness
  2. additiondiluted with water
  3. custompurified by reverse-phase HPLC [Buffer A: water

Sources & evidence

ORD record
ord-98840a78c2784ad5b7ffdd26eccb3a9c
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

Loading…