Trifluoroacetic acid → HCID 23728660, compound

HRID 534803Notes

Reaction equation

HRID 534803 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][C:12]([C:15]([N:17]([CH3:39])[C:18]2[CH:23]=[CH:22][C:21]([CH2:24][N:25]3[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[C@@H:27]([CH3:38])[CH2:26]3)=[CH:20][CH:19]=2)=[O:16])=[CH:11][CH:10]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][C:12]([C:15]([N:17]([CH3:39])[C:18]2[CH:23]=[CH:22][C:21]([CH2:24][N:25]3[CH2:30][CH2:29][NH:28][C@@H:27]([CH3:38])[CH2:26]3)=[CH:20][CH:19]=2)=[O:16])=[CH:11][CH:10]=1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59262214HCID 59262214, compound

Product 1

HCID 23728660HCID 23728660, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl (2S)-4-({4-[{[6-(2-cyanophenyl)-3-pyridinyl]carbonyl}(methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate (D49) (0.091 g, 0.173 mmol) was stirred in DCM (10 mL) and TFA (2.5 mL) was added drop-wise. The reaction mixture was stirred for ˜1 h, then concentrated in vacuo and re-diluted with DCM and water. The separated aqueous layer was basified to pH14 with concentrated NaOH solution, then extracted with DCM which was dried (Na2SO4) and concentrated to give the crude product which was purified by column chromatography. Elution with 0-10% MeOH/DCM yielded the title compound as a colourless oil (0.054 g). δH (CDCl3, 400 MHz) 8.59 (1H, s), 7.83 (1H, dd), 7.78 (2H, m), 7.67 (1H, m), 7.50 (1H, m), 7.23 (2H, d), 7.05 (2H, d), 3.54 (3H, s), 3.45 (2H, s), 2.89-3.02 (3H, m), 2.71 (2H, m), 2.09 (1H, t), 1.79 (1H, t), 1.75 (br.s) 1.07 (3H, d). MS (ES): MH+ 426.2.

Workup

  1. concentrationconcentrated in vacuo
  2. additionre-diluted with DCM and water
  3. extractionextracted with DCM which
  4. dry with materialwas dried (Na2SO4)
  5. concentrationconcentrated
  6. customto give the crude product which
  7. customwas purified by column chromatography
  8. washElution with 0-10% MeOH/DCM

Sources & evidence

ORD record
ord-f6669e2002e743009c9393ac22342e5b
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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